功能化季铵盐在水介质中的Suzuki和Heck反应的应用研究
|
摘要
Suzuki反应和Heck反应是现代有机合成中重要的反应,在天然产物、医药和高分子的合成中有着极其重要的地位。近年来,水相中的C-C偶联反应受到了越来越多研究者的关注。我们将同时具有配位功能和相转移作用的功能化季铵盐卤化1-烷基-4-氮杂-1-氮鎓双环[2.2.2]辛烷(以下简称为DABCO季铵盐)应用于水相中的Suzuki和Heck偶联反应。主要内容包括以下四章：
第一章概述了水相中Suzuki反应和Heck反应的研究进展及课题提出的意义。
第二章采用水为反应介质,在溴化1-丁基-4-氮杂-1-氮鎓双环[2.2.2]辛烷([BDABCO]Br)存在下,纳米钯能有效地催化一系列卤代芳烃与芳基硼酸发生Suzuki交叉偶联反应,以良好产率生成联苯类产物。该催化体系nano-Pd0/[BDABCO]Br/H2O对底物官能团无影响,产物可通过简单萃取分离,产率优良,对环境友好。
第三章在溴化1-十二烷基-4-氮杂-1-氮鎓双环[2.2.2]辛烷([DDABCO]Br)存在下,采用水为反应介质,纳米钯能够有效地催化Heck反应、Suzuki反应和苯硼酸的自偶联反应。nano-Pd0/[DDABCO]Br/H2O催化体系具有产率较高,稳定性好,重复使用6次,活性没有明显降低。
第四章研究了DABCO功能化二氧化硅负载纳米钯催化剂催化Suzuki反应。结果表明该催化剂能很好地催化一系列卤代芳烃与苯硼酸的Suzuki反应,以36-99%的产率生成相应的联苯化合物。该催化剂具有制备简单,催化活性好,催化反应条件温和、操作简单、产率高、可以回收利用和环境友好等特点。
The palladium catalyzed Suzuki and Heck reactions are well-established methodlogies in mordern organic synthesis. The coupling products are found to have good applications as intermediates in the preparation of natural products, medicines and polymers. We have studied the application of 1-akyl-4-aza-1-azoniabicyclo[2.2.2]octane halide in Suzuki and Heck reaction. This thesis is divided into four chapters.
In chapter 1, we have outlined the recently development and the significance of the Suzuki and the Heck reactions in aqueous media.
In chapter 2, a practical procedure for nano-palladium catalyzed Suzuki cross-coupling reaction in the presence of 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide ([BDABCO]Br) in water media was investigated. The combined nano-Pd0/[BDABCO]Br/H2O catalytic system exhibited excellent functional group tolerance for various aryl halides and arylboronic acids and afforded moderate to excellent yields of the corresponding biphenyl products under air conditions. This protocol provided several advantages such as excellent yield, short reaction time, simple experimental and work-up procedure, and benign to environment.
In chapter 3, a practical procedure for nano-palladium catalyzed Heck, Suzuki cross-coupling reaction and homocoupling of phenylboronic acid in the presence of 1-dodecyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide ([DDABCO]Br) in water media was investigated. The combined nano-Pd0/[DDABCO]Br/H2O catalytic system afforded good yields of the corresponding products under air conditions. Furthermore, the catalyst system can be reused for at laest 6 recycles without losing its activities.
In chapter 4, we have prepared and characterized palladium complex on the surface of silica-supported 1,4-diazabicyclo[2.2.2]octane(Pd@SiO2-DABCO), and investigated its performance in Suzuki cross-coupling reactions. The as-prepared catalyst (Pd@SiO2-DABCO) afforded 36-99% yields of the corresponding biphenyl products under air conditions. This catalyst has the advantages such as simple operation, high activity, recycling and reuse of catalysts and environmentally friend.
第一章概述了水相中Suzuki反应和Heck反应的研究进展及课题提出的意义。
第二章采用水为反应介质,在溴化1-丁基-4-氮杂-1-氮鎓双环[2.2.2]辛烷([BDABCO]Br)存在下,纳米钯能有效地催化一系列卤代芳烃与芳基硼酸发生Suzuki交叉偶联反应,以良好产率生成联苯类产物。该催化体系nano-Pd0/[BDABCO]Br/H2O对底物官能团无影响,产物可通过简单萃取分离,产率优良,对环境友好。
第三章在溴化1-十二烷基-4-氮杂-1-氮鎓双环[2.2.2]辛烷([DDABCO]Br)存在下,采用水为反应介质,纳米钯能够有效地催化Heck反应、Suzuki反应和苯硼酸的自偶联反应。nano-Pd0/[DDABCO]Br/H2O催化体系具有产率较高,稳定性好,重复使用6次,活性没有明显降低。
第四章研究了DABCO功能化二氧化硅负载纳米钯催化剂催化Suzuki反应。结果表明该催化剂能很好地催化一系列卤代芳烃与苯硼酸的Suzuki反应,以36-99%的产率生成相应的联苯化合物。该催化剂具有制备简单,催化活性好,催化反应条件温和、操作简单、产率高、可以回收利用和环境友好等特点。
The palladium catalyzed Suzuki and Heck reactions are well-established methodlogies in mordern organic synthesis. The coupling products are found to have good applications as intermediates in the preparation of natural products, medicines and polymers. We have studied the application of 1-akyl-4-aza-1-azoniabicyclo[2.2.2]octane halide in Suzuki and Heck reaction. This thesis is divided into four chapters.
In chapter 1, we have outlined the recently development and the significance of the Suzuki and the Heck reactions in aqueous media.
In chapter 2, a practical procedure for nano-palladium catalyzed Suzuki cross-coupling reaction in the presence of 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide ([BDABCO]Br) in water media was investigated. The combined nano-Pd0/[BDABCO]Br/H2O catalytic system exhibited excellent functional group tolerance for various aryl halides and arylboronic acids and afforded moderate to excellent yields of the corresponding biphenyl products under air conditions. This protocol provided several advantages such as excellent yield, short reaction time, simple experimental and work-up procedure, and benign to environment.
In chapter 3, a practical procedure for nano-palladium catalyzed Heck, Suzuki cross-coupling reaction and homocoupling of phenylboronic acid in the presence of 1-dodecyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide ([DDABCO]Br) in water media was investigated. The combined nano-Pd0/[DDABCO]Br/H2O catalytic system afforded good yields of the corresponding products under air conditions. Furthermore, the catalyst system can be reused for at laest 6 recycles without losing its activities.
In chapter 4, we have prepared and characterized palladium complex on the surface of silica-supported 1,4-diazabicyclo[2.2.2]octane(Pd@SiO2-DABCO), and investigated its performance in Suzuki cross-coupling reactions. The as-prepared catalyst (Pd@SiO2-DABCO) afforded 36-99% yields of the corresponding biphenyl products under air conditions. This catalyst has the advantages such as simple operation, high activity, recycling and reuse of catalysts and environmentally friend.
引文
[1]Miyaura N, Yanagi T, Suzuki A. The palladium-catalyzed cross-coupling reaction of phenylboronic acid with haloarenes in the presebce of bases[J]. Synth. Commun.,1981, 11(7):513-515.
[2]Heck R F, Nolley J P. Palladium-catalyzed vinylie hydrogen substitution reaetion with aryl, benzyl, and styryl halides[J]. J. Org. Chem.,1972,37(14):2320-2322.
[3]Mizoroki T, Mori K, Ozaki A. Arylation of olefin with aryl iodide catalyzed by palladium[J]. Bull. Chem. Soc. Jpn.,1971,44(2):581-587.
[4]Negshi E I. Selective carbon-carbon bond formation via transition metal catalysis:ahighly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel-or palladium-catalyzed reactions of aryl-and benzylzinc derivatives with aryl halides[J]. J. Org. Chem.,1977,42(10):1821-1830.
[5]Tamao K, Sumitani K, Kumada M. Selective carbon-carbon bond formation by cross-coupling of grignard reagents with organic halides. catalysis by nickel-phosphine complexes[J]. J. Am. Chem. Soc,1972,94(12):4374-4377.
[6]Stille J K. The palladium catalyzed cross-coupling reactions of organotin reagents with organic electrophiles[J]. Angew. Chem. Int. Ed.,1986,25(6):508-524.
[7]Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds[J]. Chem. Rev.,1995,95(7):2457-2483.
[8]Hassan J, Srvign M, Gozzi C. Aryl-aryl bond formation one century after the diseovery of the Ullmann reaetion[J].Chem.Rev.,2002,102(5):1359-1470.
[9]周少林,徐利文,夏春谷,等.Suzuki偶联反应的最新研究进展[J].有机化学．2004,24(12)：1501-1512.
[10]Zapf A. Novel substrates for palladium-catalyzed coupling reactions of arene[J]. Angew. Chem. Int. Ed.,2003,42(44):5394-5399.
[11]Cho C S, Itotani K, Uemara S. Sodium tetraphenylborate as a phenylating reagent in the palladium-catalyzed phenylation of alkenes and acid chlorides[J]. J. Orgnomet. Chem., 1993,443(2):253-259.
[12]Bmnagin N A, Korolev D N. Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes[J]. Tetrahedron Lett.,1999,40 (15): 3057-3060.
[13]Bandgar B P, Patil A V. A rapid, solvent-free, ligandless and mild method for preparing aromatic ketones from acyl chlorides and arylboronic acids via a Suzuki-Miyaura type of coupling reaction[J]. Tetrahedron Lett.,2005,46 (44):7627-7630.
[14]辛炳炜.在聚乙二醇一水体系中合成二苯甲酮[J].化学通报,2008,(4)：303-307.
[15]Chowdhury S, Georghiou P E. Palladium catalyzed cross-coupling between phenyl-or naphthylboronic acids and benzylic bromides[J]. Tetrahedron Lett.,1999,40(43): 7599-7603.
[16]Bandgar B P, Bettigeri S V, Phopase J. Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with aryl boronic acids under mild conditions[J]. Tetrahedron Lett.,2004,45 (37):6959-6962.
[17]Burns M J, Fairlamb I J S, Kapdi A R, Sehnal P, Taylor R J K. Simple palladium(II) precatalyst for Suzuki-Miyaura couplings:efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners[J]. Org. Lett.,2007,9(26):5397-5400.
[18]Kuwano R, Yokogi M. Suzuki-Miyaura cross-coupling of benzylic carbonates with arylboronic acids[J]. Org. Lett.,2005,7(5):945-947.
[19]Yamamoto T, Ohta T, Ito Y. Palladium-Catalyzed Addition of Arylboronic Acids to Aldehydes[J]. Org. Lett.,2005,7(19):4153-4155.
[20]Lin S H, Lu X Y. Cationic Pd(Ⅱ)/Bipyridine-Catalyzed addition of arylboronic acids to arylaldehydes. One-pot synthesis of unsymmetrical triarylmethanes[J]. J. Org. Chem.,2007, 72(25):9757-9760.
[21]Kuriyama M, Shimazawa R, Shirai R. Efficient 1,2-addition of aryl-and alkenylboronic acids to aldehydes catalyzed by the palladium/thioether imidazolinium chloride system[J]. J. Org. Chem.,2008,73(4):1597-1600.
[22]Yu A J, Cheng B L, Wu Y J, Li J Y, Wei K. Cyclopalladated complexes catalyzed addition of arylboronic acids to aldehydes in neat water[J]. Tetrahedron Lett.,2008,49(37):5405-5407.
[23]Leadbeater N E. Fast, easy, clean chemistry by using water as a solvent and microwave heating:the Suzuki coupling as an illustration[J]. Chem. Commun.,2005,23:2881-2902.
[24]Bumagin N A, Bykov V V. Ligandless palladium catalyzed reactions of arylboronic acids and sodium tetraphenylborate with aryl halides in aqueous media [J]. Tetrahedron 1997, 53(42):14437-14450.
[25]Villemin D, Gomez-E M J, Saint-Clair J F. Palladium-catalysed phenylation of heteroaromatics in water or methylformamide under microwave irradiation[J]. Tetrahedron Lett.,42(4):635-637.
[26]Casalnuovo A L, Calabrese J C. Palladium-catalyzed alkylations in aqueous media[J]. J. Am. Chem. Soc,1990,112(11):4324-4330.
[27]Leadbeater N E. Fast, easy, clean chemistry by using water as a solvent and microwave heating:the Suzuki coupling as an illustration[J]. Chem. Commun.,2005,23:2881-2902.
[28]Guo X M, Zhou J, Li X Y, Sun H J. Synthesis and catalytic applications of sulfonate [3-ketoimine and [3-diimine in the Suzuki reaction in aqueous phase[J]. J. Organometal. Chem.,2008,693(25):3692-3696.
[29]Zhou J, Li X Y, Sun H J. An efficient and recyclable water-soluble cyclopalladated complex for aqueous Suzuki reactions under aerial conditions[J]. J. Organometal. Chem.,2010, 695(2):297-303.
[30]Chalker J M, Wood C S C, Davis B G. A Convenient catalyst for aqueous and protein Suzuki-Miyaura cross-coupling[J]. J. Am. Chem. Soc,2009,131(45):16346-16347.
[31]姜岚,李争宁,赵德峰.Pd-N-杂环卡宾化合物催化的Heck反应、Suzuki反应进展[J].有机化学.2010,30(2)：200-210.
[32]Karimi B, Akhavan P F. Main-chain NHC-palladium polymer as a recyclable self-supported catalyst in the Suzuki-Miyaura coupling of aryl chlorides in water[J]. Chem. Commun., 2009,25:3750-3752.
[33]Turkmen H, Can R, Cetinkaya B. Aqueous-phase Suzuki-Miyaura cross-coupling reactions catalyzed by Pd-NHC complexes [J]. Dalton Trans.,2009,35:7039-7044.
[34]辛炳炜.水-TBAB体系中Suzuki偶联反应研究进展[J].河西学院学报。2007,20(5)：34-38.
[35]Badone D, Baroni M, Cardamone R, Ielmini A, Guzzi U. Highly efficient palladium-catalyzed boronic acid coupling reactions in water:scope and limitations[J]. J. Org. Chem.,1997,62(21):7170-7173.
[36]Leadbeater N E, Marco M. Ligand-free palladium catalysis of the Suzuki reaction in water using microwave heating[J]. Org. Lett.,2002,4(17):2973-2976.
[37]Chen C L, Liu Y H, Peng S M, Liu S T. An effcient catalyst for Suzuki-Miyaura coupling reactionin aqueous medium under aerobic conditions[J]. Tetrahedron Lett.,2005,46(3): 521-523.
[38]Ma J, Cui X L, Gao L Y, Wu Y J. Ferrocenylimidazoline palladacycles:Syntheses, crystal structures and applications as catalysts for Suzuki cross coupling reaction in water[J]. Inorg. Chem. Comm.,2007,10(7):762-766.
[39]Bai L. Atom-efficient coupling reaction of aryl bromides with sodium tetraphenylborate catalyzed by reusable Pd/C in water under focused microwave irradiation[J]. Chin. Chem. Lett.,2009,20(2):158-160.
[40]Denicourt N A, Romagne M L, Roucoux A. N-(2-hydroxyethyl)ammonium derivatives as protective agents for Pd(0) nanocolloids and catalytic investigation in Suzuki reactions in aqueous media. Catal. Comm.,2008,10(1):68-70.
[41]Liu L F, Zhang Y H, Wang Y G. Phosphine-Free palladium acetate catalyzed Suzuki reaction in water[J]. J. Org. Chem.,2005,70(15):6122-6125.
[42]Uozumi Y, Nakai Y. An Amphiphilic resin-supported palladium catalyst for high-throughput cross-coupling in water[J]. Org. Lett.,2002,4(17):2997-3000.
[43]Zhang M C, Zhang W Q. Pd nanoparticles immobilized on pH-responsive and chelating nanospheres as an efficient and recyclable catalyst for Suzuki reaction in water[J]. J. Phys. Chem. C,2008,112(16):6245-6252.
[44]Lyubimov S E, KorlyukovA A, Pisarev S A, Matveev V V, Chalykh A E, Zlotin S G, Davankov V A. Palladium-containing hypercrosslinked polystyrene as an easy to prepare catalyst for Suzuki reaction in water and organic solvents[J]. React. Funct. Polym.,2009,69 (10):755-758.
[45]Yi S S, Lee D H, Sin E Y, Lee Y S. Chitosan-supported palladium(0) catalyst for microwave-prompted Suzuki cross-coupling reaction in water[J]. Tetrahedron Lett.,2007,48 (38):6771-6775.
[46]Jin M J, Taher A, Kang H J, Choi M, Ryoo R. Palladium acetate immobilized in a hierarchical MFI zeolite-supported ionic liquid:a highly active and recyclable catalyst for Suzuki reaction in water[J]. Green Chem.,2009, (11):309-313.
[47]Wei J F, Jiao J, Feng J J, Lv J, Zhang X R, Shi X Y, Chen Z G. PdEDTA held in an ionic liquid brush as a highly efficient and reusable catalyst for Suzuki reactions in water[J]. J. Org. Chem.,2009,74(16):6283-6286.
[48]王宗廷,张云山,王书超,夏道宏Heck反应最新研究进展[J].有机化学.2007,27(2)：143-152.
[49]Azoui H, Baczko K, Cassel S, Larpent C. Thermoregulated aqueous biphasic catalysis of Heck reactions using an amphiphilic dipyridyl-based ligand[J]. Green Chem.,2008, (10): 1197-1203.
[50]Firouzabadi H, Iranpoor N, Gholinejad M.2-Aminophenyl diphenylphosphinite as a new ligand for heterogeneous palladium-catalyzed Heck-Mizoroki reactions in water in the absence of any organic co-solvent[J]. Tetrahedron 2009,65(34):7079-7084.
[51]Iranpoor N, Firouzabadi H, Tarassoli A, Fereidoonnezhad M.1,3,2,4-Diazadiphosphetidines as new P-N ligands for palladium-catalyzed Heck reaction in water[J]. Tetrahedron 2010, 66(13):2415-2421.
[52]Lamblin M, Nassar H L, Hierso J C, Fouquet E, Felpin F X. Recyclable heterogeneous palladium catalysts in pure water:Sustainable developments in Suzuki, Heck, Sonogashira and Tsuji-Trost reactions[J]. Adv. Synth. Catal.,2010,352(1):33-79.
[53]Uozumi Y, Kimura T. Heck reaction in water with amphiphilic resin-supported palladium-phosphine complexes[J]. Synlett 2002, (12):2045-2048.
[54]Qiao K, Sugimura R, Bao Q X, Tomida D, Yokoyama C. An efficient Heck reaction in water catalyzed by palladium nanoparticles immobilized on imidazolium-styrene copolymers[J]. Catal. Commun.,2008,9(15):2470-2474.
[55]Xu Y, Zhang L, Cui Y C. Catalytic performance of cellulose supported palladium complex for Heck reaction in water[J]. J. Appl. Poly. Sci.,2008,110(5):2996-3000.
[56]许英,蔡永红,崔元臣,李金金.氨基硫脲纤维素负载钯配合物的制备及其对Heck反应的催化性能[J].石油化工.2008,37(4)：328-332.
[57]许英,徐绍红,张磊,张峰,崔元臣.羧甲基纤维素负载钯催化剂的制备及对Heck反应的催化性能[J].精细化工.2008,25(11)：1083-1086.
[58]Yang Z J, Fan M J, Mu R Z, Liu W M, Liang Y M. A facile synthesis of highly functionalized dihydrofurans based on 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed reaction of halides with enones[J]. Tetrahedron 2005,61(38):9140-9146.
[59]Robiette R, Conza M, Aggarwal V K. Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes[J]. Org. Biomol. Chem.,2006,4(4):621-623.
[60]王猛,张慧,陈杰,吴小余,邓红梅,邵敏,曹卫国.氮叶立德高立体选择性地合成螺[环丙烷-1,4′-毗唑啉-5′-酮]衍生物的研究[J].有机化学.2009,29(10)：1611-1616. [1] Suzuki A. Cross-coupling reactions via organoboranes [J]. J. Organomet. Chem.,2002, 653(1-2):83-90. [2] Stanforth S P. Catalytic Cross-coupling reactions in biaryl synthesis [J].Tetrahedron 1998, 54(3-4):263-303. [3] Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds [J]. Chem. Rev.,1995,95(7):2457-2483.[4]周少林,徐利文,夏春谷,等Suzuki偶联反应的最新研究进展[J].有机化学.2004,24(12)：1501-1512.[5] Kotha S, Lahiri K, Kashinath D. Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis [J]. Tetrahedron 2002,58(48):9633-9695.[6]鞠秀萍,杜艳霞,郑韬,等.星形低分子量块状化合物的合成[J].化学研究与应用.2007,19(2)：219-223.[7]辛炳炜.离子液体-水体系中二苯甲酮的合成[J].化学研究与应用,2008,20(3)：333-336.[8] Bumagin N A, Bykov V V. Ligandless palladium catalyzed reactions of arylboronic acids and sodium tetraphenylborate with aryl halides in aqueous media [J]. Tetrahedron 1997,53(42): 14437-14450. [9] Buchard A, Komly B, Auffrant A, et al. A mixed phosphine-iminophosphorane tetradentate ligand:Synthesis, coordination to group 10 metal centers, and use as catalyst in Suzuki-Miyaura coupling [J]. Organometallics 2008,27(17):4380-4385. [10] Parisot S, Kolodziuk R, Goux-Henry C,et al. Glucosamine-based phosphines. Efficient ligands in the Suzuki cross-coupling reaction in water [J]. Tetrahedron Lett.,2002,43(41): 7397-7400.
[11]Turkmen H, Can R, Cetinkaya B. Aqueous-phase Suzuki-Miyaura cross-coupling reactions catalyzed by Pd-NHC complexes [J]. Dalton Trans.,2009,35:7039-7044.
[12]Liu P, Feng X J, He R. Salen and half-salen palladium(II) complexes:synthesis, characteriztion and catalytic activity toward Suzuki-Miyaura reaction [J]. Tetrahedron 2010, 66(3):631-636.
[13]Yamada Y M A, Takeda K, Takahashi H, et al. An assembled complex of palladium and non-cross-linked amphiphilic polymer:A highly active and recyclable catalyst for the Suzuki-Miyaura reaction [J]. Org. Lett.,2002,4(20):3371-3374.
[14]Uozumi Y, Nakai Y. An Amphiphilic resin-supported palladium catalyst for high-throughput cross-coupling in water [J]. Org. Lett.,2002,4(17):2997-3000.
[15]Zhang J, Yang F, Ren G, et al. Ultrasonic irradiation accelerated cyclopalladated ferrocenylimines catalyzed Suzuki reaction in neat water [J]. Ultrason. Sonochem.,2008, 15(2):115-118.
[16]Leadbeater N E, Marco M. Ligand-Free palladium catalysis of the Suzuki reaction in water using microwave heating [J]. Org. Lett.,2002,4(17):2973-2976.
[17]Pachon L D, Rothenberg G. Transition-metal nanoparticles:synthesis, stability and the leaching issue [J]. Appl. Organometal. Chem.,2008,22(6):288-299.
[18]Dizman B, Elasri M O, Mathias L J. Synthesis and antimicrobial activities of new water-soluble bis-quaternary ammonium methacrylate polymers [J]. J. Appl. Poly. Sci., 2004,94(2):635-642.
[19]Hsu M H, Hsu C M, Wang J C, et al. Air-stable Pd(Ⅱ) catalysts with cryptand-22 ligand for convenient and efficient Suzuki cross-coupling reactions [J]. Tetrahedron 2008,64(19): 4268-4274.
[20]Huang W, Guo J P, Xiao Y J, et al. Palladium-benzimidazolium salt catalyst systems for Suzuki coupling:development of a practical and highly active palladium catalyst system for coupling of aromatic halides with arylboronic acids [J]. Tetrahedron 2005,61(41): 9783-9790.
[21]Nunez A, Sanchez A, Burgos C, et al. Synthesis of carbo-and heterobiaryls by intermolecular radical addition of aryl bromides onto aromatic solvents [J]. Tetrahedron 2004,60(29):6217-6224.
[22]Chen S N, Wu W Y, Tsai F Y. Hiyama reaction of aryl bromides with arylsiloxanes catalyzed by a reusable palladium(Ⅱ)/cationic bipyridyl system in water [J]. Tetrahedron 2008,64(35):8164-8168.
[23]Tsai F Y, Lin B N, Chen M J, et al. Anchored palladium bipyridyl complex in nanosized MCM-41:a recyclable and efficient catalyst for the Kumada-Corriu reaction [J]. Tetrahedron,2007,63(20):4304-4309.
[1]Li C J, Chen L. Organic chemistry in water [J]. Chem. Soc. Rev.,2006,35(1):68-82.
[2]Liu S, Xiao J. Toward green catalytic synthesis-Transition metal-catalyzed reactions in non-conventional media [J]. J. Mol. Catal. A Chem.,2007,270(1-2):1-43.
[3]Li C J. Organic Reactions in aqueous media with a focus on carbon-carbon bond formations: A decade update [J]. Chem. Rev.,2005,105(8):3095-3166.
[4]Heck R F, Nolley J P J. Palladium-Catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides [J]. J. Org. Chem.,1972,37(14):2320-2322.
[5]Mizoroki T, Mori K, Ozaki A. Arylation of olefin with aryl iodide catalyzed by palladium [J]. Bull. Chem. Soc. Jpn.,1971,44(2):581-587.
[6]Firouzabadi H, Iranpoor N, Gholinejad M.2-Aminophenyl diphenylphosphinite as a new ligand for heterogeneous palladium-catalyzed Heck-Mizoroki reactions in water in the absence of any organic co-solvent[J]. Tetrahedron 2009,65(34):7079-7084.
[7]Iranpoor N, Firouzabadi H, Tarassoli A, Fereidoonnezhad M.1,3,2,4-Diazadiphosphetidines as new P-N ligands for palladium-catalyzed Heck reaction in water[J]. Tetrahedron 2010,66 (13):2415-2421.
[8]Uozumi Y, Kimura T. Heck reaction in water with amphiphilic resin-supported palladium-phosphine complexes[J]. Synlett 2002,12:2045-2048.
[9]Pachon L D, Rothenberg G. Transition-metal nanoparticles:synthesis, stability and the leaching issue [J]. Appl. Organometal. Chem.,2008,22(6):288-299.
[10]Dizman B, Elasri M O, Mathias L J. Synthesis and antimicrobial activities of new water-soluble bis-quaternary ammonium methacrylate polymers [J]. J Appl Poly Sci.,2004, 94(2):635-642.
[11]Hsu M H, Hsu C M, Wang J C, et al. Air-stable Pd(Ⅱ) catalysts with cryptand-22 ligand for convenient and efficient Suzuki cross-coupling reactions [J]. Tetrahedron 2008,64(19): 4268-4274.
[12]Tsai F Y, Lin B N, Chen M J, et al. Anchored palladium bipyridyl complex in nanosized MCM-41:a recyclable and efficient catalyst for the Kumada-Corriu reaction [J]. Tetrahedron 2007,63(20):4304-4309.
[13]Huang W, Guo J P, Xiao Y J, et al. Palladium-benzimidazolium salt catalyst systems for Suzuki coupling:development of a practical and highly active palladium catalyst system for coupling of aromatic halides with arylboronic acids [J]. Tetrahedron 2005,61(41): 9783-9790.
[14]Nunez A, Sanchez A, Burgos C, et al. Synthesis of carbo-and heterobiaryls by intermolecular radical addition of aryl bromides onto aromatic solvents [J]. Tetrahedron 2004,60(29):6217-6224.
[15]Chen S N, Wu W Y, Tsai F Y. Hiyama reaction of aryl bromides with arylsiloxanes catalyzed by reusable palladium(II)/cationic bipyridyl system in water [J]. Tetrahedron 2008,64(35):8164-8168.
[16]Zeng M F, Du Y J, Shao L J, Qi C Z, Zhang X M. Palladium-catalyzed reductive homocoupling of aromatic halides and oxidation of alcohols[J]. J. Org. Chem.,2010,75(8): 2556-2563.
[17]Ma N, Zhu Z W, Wu Y J. Cyclopalladated ferrocenylimine:a highly effective catalyst for the borylation/Suzuki coupling reaction [J]. Tetrahedron 2007,63(22):4625-4629.
[1]Suzuki A. Cross-coupling reactions via organoboranes[J]. J. Organomet. Chem.,2002, 653(1-2):83-90.
[2]Stanforth S P. Catalytic cross-coupling reactions in biaryl synthesis[J]. Tetrahedron 1998, 54(3-4):263-303.
[3]Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds[J]. Chem. Rev.,1995,95(7):2457-2483.
[4]Uozumi Y, Nakai Y. An Amphiphilic resin-supported palladium catalyst for high-throughput cross-coupling in water[J]. Org. Lett.,2002,4(17):2997-3000.
[5]Zhang M C, Zhang W Q. Pd nanoparticles immobilized on pH-responsive and chelating nanospheres as an efficient and recyclable catalyst for Suzuki reaction in water[J]. J. Phys. Chem. C.,2008,112(16):6245-6252.
[6]Lyubimov S E, Korlyukov A A, Pisarev S A, Matveev V V, Chalykh A E, Zlotin S G, Davankov V A. Palladium-containing hypercrosslinked polystyrene as an easy to prepare catalyst for Suzuki reaction in water and organic solvents[J]. React. Funct. Polym.,2009,69 (10):755-758.
[7]Yi S S, Lee D H, Sin E Y, Lee Y S. Chitosan-supported palladium(0) catalyst for microwave-prompted Suzuki cross-coupling reaction in water[J]. Tetrahedron Lett.,2007,48 (38):6771-6775.
[8]Jiang N, Ragauskas A J. Environmentally friendly synthesis of biaryls:Suzuki reaction of aryl bromides in water at low catalyst loadings[J]. Tetrahedron Lett.,2006,47(2):197-200.
[9]Jin M J, Taher A, Kang H J, Choi M, Ryoo R. Palladium acetate immobilized in a hierarchicalMFI zeolite-supported ionic liquid:a highly active and recyclable catalyst for Suzuki reaction in water[J]. Green Chem.,2009, (11):309-313.
[10]Wei J F, Jiao J, Feng J J, Lv J, Zhang X R, Shi X Y, Chen Z G. PdEDTA held in an ionic liquid brush as a highly efficient and reusable catalyst for Suzuki reactions in water[J]. J. Org. Chem.,2009,74(16):6283-6286.
[11]Das D D, Sayari A. Applications of pore-expanded mesoporous silica 6. Novel synthesis of monodispersed supported palladium nanoparticles and their catalytic activity for Suzuki reaction[J]. J. Catal.,2007,246(1):60-65.
[12]Tzschucke C C, Andrushko V, Bannwarth W. Assessment of the reusability of Pd complexes supported on fluorous silica gel as catalysts for Suzuki couplings[J]. Eur. J. Org. Chem., 2005, (24):5248-5261.
[13]Wang L, Cai Chun. Fluorous silicagel-supported peruoro-tagged palladium nanoparticles catalyze Suzuki cross-coupling reaction in water[J]. J. Mol. Catal.A-Chem.,2009,306(1-2): 97-101.
[14]Sayah R.; Glegola K.; Framery E.; Dufaud V. Suzuki-Miyaura reactions of aryl chloride derivatives with arylboronic acids using mesoporous silica-supported aryl-dicyclohexylphosphine[J]. Adv. Synth. Catal.,2007,349(3):373-381.
[15]Karimi B, Elhamifar D, Clark J H, Hunt A J. Ordered mesoporous organosilica with ionic-liquid framework:An efficient and reusable support for the palladium-catalyzed Suzuki-Miyaura coupling reaction in water[J]. Chem. Eur. J.,2010,16(27):8047-8053.
[16]Liu J, Li Y Q, Zheng W J. Synthesis of immobilized nanopalladium on polymer-supported Schiff base, and study of its catalytic activity in the Suzuki-Miyaura reaction[J]. Monatsh Chem.,2009,140(12):1425-1429.
[17]Huang X J, Dong F, Chen L, Li Y Q. Nanopalladium immobilized on aminoethanol-functionalized poly(vinyl chloride):an easily prepared, air and moisture stable catalyst for Heck reactions[J]. Monatsh Chem.,2008,139(12):1447-1451.
[18]Schweizer S, Becht J M. Drian, C. L. Highly efficient reusable polymer-supported Pd catalysts of general use for the Suzuki reaction[J]. Tetrahedron 2010,66(3):765-772.
[19]Zhou W J, Wang K H, Wang J X, Gao Z R. Ligand-free, atom-efcient Suzuki-Miyaura type cross-coupling reactions at room temperature[J]. Tetrahedron 2010,66(38):7633-7641.
[2]Heck R F, Nolley J P. Palladium-catalyzed vinylie hydrogen substitution reaetion with aryl, benzyl, and styryl halides[J]. J. Org. Chem.,1972,37(14):2320-2322.
[3]Mizoroki T, Mori K, Ozaki A. Arylation of olefin with aryl iodide catalyzed by palladium[J]. Bull. Chem. Soc. Jpn.,1971,44(2):581-587.
[4]Negshi E I. Selective carbon-carbon bond formation via transition metal catalysis:ahighly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel-or palladium-catalyzed reactions of aryl-and benzylzinc derivatives with aryl halides[J]. J. Org. Chem.,1977,42(10):1821-1830.
[5]Tamao K, Sumitani K, Kumada M. Selective carbon-carbon bond formation by cross-coupling of grignard reagents with organic halides. catalysis by nickel-phosphine complexes[J]. J. Am. Chem. Soc,1972,94(12):4374-4377.
[6]Stille J K. The palladium catalyzed cross-coupling reactions of organotin reagents with organic electrophiles[J]. Angew. Chem. Int. Ed.,1986,25(6):508-524.
[7]Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds[J]. Chem. Rev.,1995,95(7):2457-2483.
[8]Hassan J, Srvign M, Gozzi C. Aryl-aryl bond formation one century after the diseovery of the Ullmann reaetion[J].Chem.Rev.,2002,102(5):1359-1470.
[9]周少林,徐利文,夏春谷,等.Suzuki偶联反应的最新研究进展[J].有机化学．2004,24(12)：1501-1512.
[10]Zapf A. Novel substrates for palladium-catalyzed coupling reactions of arene[J]. Angew. Chem. Int. Ed.,2003,42(44):5394-5399.
[11]Cho C S, Itotani K, Uemara S. Sodium tetraphenylborate as a phenylating reagent in the palladium-catalyzed phenylation of alkenes and acid chlorides[J]. J. Orgnomet. Chem., 1993,443(2):253-259.
[12]Bmnagin N A, Korolev D N. Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes[J]. Tetrahedron Lett.,1999,40 (15): 3057-3060.
[13]Bandgar B P, Patil A V. A rapid, solvent-free, ligandless and mild method for preparing aromatic ketones from acyl chlorides and arylboronic acids via a Suzuki-Miyaura type of coupling reaction[J]. Tetrahedron Lett.,2005,46 (44):7627-7630.
[14]辛炳炜.在聚乙二醇一水体系中合成二苯甲酮[J].化学通报,2008,(4)：303-307.
[15]Chowdhury S, Georghiou P E. Palladium catalyzed cross-coupling between phenyl-or naphthylboronic acids and benzylic bromides[J]. Tetrahedron Lett.,1999,40(43): 7599-7603.
[16]Bandgar B P, Bettigeri S V, Phopase J. Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with aryl boronic acids under mild conditions[J]. Tetrahedron Lett.,2004,45 (37):6959-6962.
[17]Burns M J, Fairlamb I J S, Kapdi A R, Sehnal P, Taylor R J K. Simple palladium(II) precatalyst for Suzuki-Miyaura couplings:efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners[J]. Org. Lett.,2007,9(26):5397-5400.
[18]Kuwano R, Yokogi M. Suzuki-Miyaura cross-coupling of benzylic carbonates with arylboronic acids[J]. Org. Lett.,2005,7(5):945-947.
[19]Yamamoto T, Ohta T, Ito Y. Palladium-Catalyzed Addition of Arylboronic Acids to Aldehydes[J]. Org. Lett.,2005,7(19):4153-4155.
[20]Lin S H, Lu X Y. Cationic Pd(Ⅱ)/Bipyridine-Catalyzed addition of arylboronic acids to arylaldehydes. One-pot synthesis of unsymmetrical triarylmethanes[J]. J. Org. Chem.,2007, 72(25):9757-9760.
[21]Kuriyama M, Shimazawa R, Shirai R. Efficient 1,2-addition of aryl-and alkenylboronic acids to aldehydes catalyzed by the palladium/thioether imidazolinium chloride system[J]. J. Org. Chem.,2008,73(4):1597-1600.
[22]Yu A J, Cheng B L, Wu Y J, Li J Y, Wei K. Cyclopalladated complexes catalyzed addition of arylboronic acids to aldehydes in neat water[J]. Tetrahedron Lett.,2008,49(37):5405-5407.
[23]Leadbeater N E. Fast, easy, clean chemistry by using water as a solvent and microwave heating:the Suzuki coupling as an illustration[J]. Chem. Commun.,2005,23:2881-2902.
[24]Bumagin N A, Bykov V V. Ligandless palladium catalyzed reactions of arylboronic acids and sodium tetraphenylborate with aryl halides in aqueous media [J]. Tetrahedron 1997, 53(42):14437-14450.
[25]Villemin D, Gomez-E M J, Saint-Clair J F. Palladium-catalysed phenylation of heteroaromatics in water or methylformamide under microwave irradiation[J]. Tetrahedron Lett.,42(4):635-637.
[26]Casalnuovo A L, Calabrese J C. Palladium-catalyzed alkylations in aqueous media[J]. J. Am. Chem. Soc,1990,112(11):4324-4330.
[27]Leadbeater N E. Fast, easy, clean chemistry by using water as a solvent and microwave heating:the Suzuki coupling as an illustration[J]. Chem. Commun.,2005,23:2881-2902.
[28]Guo X M, Zhou J, Li X Y, Sun H J. Synthesis and catalytic applications of sulfonate [3-ketoimine and [3-diimine in the Suzuki reaction in aqueous phase[J]. J. Organometal. Chem.,2008,693(25):3692-3696.
[29]Zhou J, Li X Y, Sun H J. An efficient and recyclable water-soluble cyclopalladated complex for aqueous Suzuki reactions under aerial conditions[J]. J. Organometal. Chem.,2010, 695(2):297-303.
[30]Chalker J M, Wood C S C, Davis B G. A Convenient catalyst for aqueous and protein Suzuki-Miyaura cross-coupling[J]. J. Am. Chem. Soc,2009,131(45):16346-16347.
[31]姜岚,李争宁,赵德峰.Pd-N-杂环卡宾化合物催化的Heck反应、Suzuki反应进展[J].有机化学.2010,30(2)：200-210.
[32]Karimi B, Akhavan P F. Main-chain NHC-palladium polymer as a recyclable self-supported catalyst in the Suzuki-Miyaura coupling of aryl chlorides in water[J]. Chem. Commun., 2009,25:3750-3752.
[33]Turkmen H, Can R, Cetinkaya B. Aqueous-phase Suzuki-Miyaura cross-coupling reactions catalyzed by Pd-NHC complexes [J]. Dalton Trans.,2009,35:7039-7044.
[34]辛炳炜.水-TBAB体系中Suzuki偶联反应研究进展[J].河西学院学报。2007,20(5)：34-38.
[35]Badone D, Baroni M, Cardamone R, Ielmini A, Guzzi U. Highly efficient palladium-catalyzed boronic acid coupling reactions in water:scope and limitations[J]. J. Org. Chem.,1997,62(21):7170-7173.
[36]Leadbeater N E, Marco M. Ligand-free palladium catalysis of the Suzuki reaction in water using microwave heating[J]. Org. Lett.,2002,4(17):2973-2976.
[37]Chen C L, Liu Y H, Peng S M, Liu S T. An effcient catalyst for Suzuki-Miyaura coupling reactionin aqueous medium under aerobic conditions[J]. Tetrahedron Lett.,2005,46(3): 521-523.
[38]Ma J, Cui X L, Gao L Y, Wu Y J. Ferrocenylimidazoline palladacycles:Syntheses, crystal structures and applications as catalysts for Suzuki cross coupling reaction in water[J]. Inorg. Chem. Comm.,2007,10(7):762-766.
[39]Bai L. Atom-efficient coupling reaction of aryl bromides with sodium tetraphenylborate catalyzed by reusable Pd/C in water under focused microwave irradiation[J]. Chin. Chem. Lett.,2009,20(2):158-160.
[40]Denicourt N A, Romagne M L, Roucoux A. N-(2-hydroxyethyl)ammonium derivatives as protective agents for Pd(0) nanocolloids and catalytic investigation in Suzuki reactions in aqueous media. Catal. Comm.,2008,10(1):68-70.
[41]Liu L F, Zhang Y H, Wang Y G. Phosphine-Free palladium acetate catalyzed Suzuki reaction in water[J]. J. Org. Chem.,2005,70(15):6122-6125.
[42]Uozumi Y, Nakai Y. An Amphiphilic resin-supported palladium catalyst for high-throughput cross-coupling in water[J]. Org. Lett.,2002,4(17):2997-3000.
[43]Zhang M C, Zhang W Q. Pd nanoparticles immobilized on pH-responsive and chelating nanospheres as an efficient and recyclable catalyst for Suzuki reaction in water[J]. J. Phys. Chem. C,2008,112(16):6245-6252.
[44]Lyubimov S E, KorlyukovA A, Pisarev S A, Matveev V V, Chalykh A E, Zlotin S G, Davankov V A. Palladium-containing hypercrosslinked polystyrene as an easy to prepare catalyst for Suzuki reaction in water and organic solvents[J]. React. Funct. Polym.,2009,69 (10):755-758.
[45]Yi S S, Lee D H, Sin E Y, Lee Y S. Chitosan-supported palladium(0) catalyst for microwave-prompted Suzuki cross-coupling reaction in water[J]. Tetrahedron Lett.,2007,48 (38):6771-6775.
[46]Jin M J, Taher A, Kang H J, Choi M, Ryoo R. Palladium acetate immobilized in a hierarchical MFI zeolite-supported ionic liquid:a highly active and recyclable catalyst for Suzuki reaction in water[J]. Green Chem.,2009, (11):309-313.
[47]Wei J F, Jiao J, Feng J J, Lv J, Zhang X R, Shi X Y, Chen Z G. PdEDTA held in an ionic liquid brush as a highly efficient and reusable catalyst for Suzuki reactions in water[J]. J. Org. Chem.,2009,74(16):6283-6286.
[48]王宗廷,张云山,王书超,夏道宏Heck反应最新研究进展[J].有机化学.2007,27(2)：143-152.
[49]Azoui H, Baczko K, Cassel S, Larpent C. Thermoregulated aqueous biphasic catalysis of Heck reactions using an amphiphilic dipyridyl-based ligand[J]. Green Chem.,2008, (10): 1197-1203.
[50]Firouzabadi H, Iranpoor N, Gholinejad M.2-Aminophenyl diphenylphosphinite as a new ligand for heterogeneous palladium-catalyzed Heck-Mizoroki reactions in water in the absence of any organic co-solvent[J]. Tetrahedron 2009,65(34):7079-7084.
[51]Iranpoor N, Firouzabadi H, Tarassoli A, Fereidoonnezhad M.1,3,2,4-Diazadiphosphetidines as new P-N ligands for palladium-catalyzed Heck reaction in water[J]. Tetrahedron 2010, 66(13):2415-2421.
[52]Lamblin M, Nassar H L, Hierso J C, Fouquet E, Felpin F X. Recyclable heterogeneous palladium catalysts in pure water:Sustainable developments in Suzuki, Heck, Sonogashira and Tsuji-Trost reactions[J]. Adv. Synth. Catal.,2010,352(1):33-79.
[53]Uozumi Y, Kimura T. Heck reaction in water with amphiphilic resin-supported palladium-phosphine complexes[J]. Synlett 2002, (12):2045-2048.
[54]Qiao K, Sugimura R, Bao Q X, Tomida D, Yokoyama C. An efficient Heck reaction in water catalyzed by palladium nanoparticles immobilized on imidazolium-styrene copolymers[J]. Catal. Commun.,2008,9(15):2470-2474.
[55]Xu Y, Zhang L, Cui Y C. Catalytic performance of cellulose supported palladium complex for Heck reaction in water[J]. J. Appl. Poly. Sci.,2008,110(5):2996-3000.
[56]许英,蔡永红,崔元臣,李金金.氨基硫脲纤维素负载钯配合物的制备及其对Heck反应的催化性能[J].石油化工.2008,37(4)：328-332.
[57]许英,徐绍红,张磊,张峰,崔元臣.羧甲基纤维素负载钯催化剂的制备及对Heck反应的催化性能[J].精细化工.2008,25(11)：1083-1086.
[58]Yang Z J, Fan M J, Mu R Z, Liu W M, Liang Y M. A facile synthesis of highly functionalized dihydrofurans based on 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed reaction of halides with enones[J]. Tetrahedron 2005,61(38):9140-9146.
[59]Robiette R, Conza M, Aggarwal V K. Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes[J]. Org. Biomol. Chem.,2006,4(4):621-623.
[60]王猛,张慧,陈杰,吴小余,邓红梅,邵敏,曹卫国.氮叶立德高立体选择性地合成螺[环丙烷-1,4′-毗唑啉-5′-酮]衍生物的研究[J].有机化学.2009,29(10)：1611-1616. [1] Suzuki A. Cross-coupling reactions via organoboranes [J]. J. Organomet. Chem.,2002, 653(1-2):83-90. [2] Stanforth S P. Catalytic Cross-coupling reactions in biaryl synthesis [J].Tetrahedron 1998, 54(3-4):263-303. [3] Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds [J]. Chem. Rev.,1995,95(7):2457-2483.[4]周少林,徐利文,夏春谷,等Suzuki偶联反应的最新研究进展[J].有机化学.2004,24(12)：1501-1512.[5] Kotha S, Lahiri K, Kashinath D. Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis [J]. Tetrahedron 2002,58(48):9633-9695.[6]鞠秀萍,杜艳霞,郑韬,等.星形低分子量块状化合物的合成[J].化学研究与应用.2007,19(2)：219-223.[7]辛炳炜.离子液体-水体系中二苯甲酮的合成[J].化学研究与应用,2008,20(3)：333-336.[8] Bumagin N A, Bykov V V. Ligandless palladium catalyzed reactions of arylboronic acids and sodium tetraphenylborate with aryl halides in aqueous media [J]. Tetrahedron 1997,53(42): 14437-14450. [9] Buchard A, Komly B, Auffrant A, et al. A mixed phosphine-iminophosphorane tetradentate ligand:Synthesis, coordination to group 10 metal centers, and use as catalyst in Suzuki-Miyaura coupling [J]. Organometallics 2008,27(17):4380-4385. [10] Parisot S, Kolodziuk R, Goux-Henry C,et al. Glucosamine-based phosphines. Efficient ligands in the Suzuki cross-coupling reaction in water [J]. Tetrahedron Lett.,2002,43(41): 7397-7400.
[11]Turkmen H, Can R, Cetinkaya B. Aqueous-phase Suzuki-Miyaura cross-coupling reactions catalyzed by Pd-NHC complexes [J]. Dalton Trans.,2009,35:7039-7044.
[12]Liu P, Feng X J, He R. Salen and half-salen palladium(II) complexes:synthesis, characteriztion and catalytic activity toward Suzuki-Miyaura reaction [J]. Tetrahedron 2010, 66(3):631-636.
[13]Yamada Y M A, Takeda K, Takahashi H, et al. An assembled complex of palladium and non-cross-linked amphiphilic polymer:A highly active and recyclable catalyst for the Suzuki-Miyaura reaction [J]. Org. Lett.,2002,4(20):3371-3374.
[14]Uozumi Y, Nakai Y. An Amphiphilic resin-supported palladium catalyst for high-throughput cross-coupling in water [J]. Org. Lett.,2002,4(17):2997-3000.
[15]Zhang J, Yang F, Ren G, et al. Ultrasonic irradiation accelerated cyclopalladated ferrocenylimines catalyzed Suzuki reaction in neat water [J]. Ultrason. Sonochem.,2008, 15(2):115-118.
[16]Leadbeater N E, Marco M. Ligand-Free palladium catalysis of the Suzuki reaction in water using microwave heating [J]. Org. Lett.,2002,4(17):2973-2976.
[17]Pachon L D, Rothenberg G. Transition-metal nanoparticles:synthesis, stability and the leaching issue [J]. Appl. Organometal. Chem.,2008,22(6):288-299.
[18]Dizman B, Elasri M O, Mathias L J. Synthesis and antimicrobial activities of new water-soluble bis-quaternary ammonium methacrylate polymers [J]. J. Appl. Poly. Sci., 2004,94(2):635-642.
[19]Hsu M H, Hsu C M, Wang J C, et al. Air-stable Pd(Ⅱ) catalysts with cryptand-22 ligand for convenient and efficient Suzuki cross-coupling reactions [J]. Tetrahedron 2008,64(19): 4268-4274.
[20]Huang W, Guo J P, Xiao Y J, et al. Palladium-benzimidazolium salt catalyst systems for Suzuki coupling:development of a practical and highly active palladium catalyst system for coupling of aromatic halides with arylboronic acids [J]. Tetrahedron 2005,61(41): 9783-9790.
[21]Nunez A, Sanchez A, Burgos C, et al. Synthesis of carbo-and heterobiaryls by intermolecular radical addition of aryl bromides onto aromatic solvents [J]. Tetrahedron 2004,60(29):6217-6224.
[22]Chen S N, Wu W Y, Tsai F Y. Hiyama reaction of aryl bromides with arylsiloxanes catalyzed by a reusable palladium(Ⅱ)/cationic bipyridyl system in water [J]. Tetrahedron 2008,64(35):8164-8168.
[23]Tsai F Y, Lin B N, Chen M J, et al. Anchored palladium bipyridyl complex in nanosized MCM-41:a recyclable and efficient catalyst for the Kumada-Corriu reaction [J]. Tetrahedron,2007,63(20):4304-4309.
[1]Li C J, Chen L. Organic chemistry in water [J]. Chem. Soc. Rev.,2006,35(1):68-82.
[2]Liu S, Xiao J. Toward green catalytic synthesis-Transition metal-catalyzed reactions in non-conventional media [J]. J. Mol. Catal. A Chem.,2007,270(1-2):1-43.
[3]Li C J. Organic Reactions in aqueous media with a focus on carbon-carbon bond formations: A decade update [J]. Chem. Rev.,2005,105(8):3095-3166.
[4]Heck R F, Nolley J P J. Palladium-Catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides [J]. J. Org. Chem.,1972,37(14):2320-2322.
[5]Mizoroki T, Mori K, Ozaki A. Arylation of olefin with aryl iodide catalyzed by palladium [J]. Bull. Chem. Soc. Jpn.,1971,44(2):581-587.
[6]Firouzabadi H, Iranpoor N, Gholinejad M.2-Aminophenyl diphenylphosphinite as a new ligand for heterogeneous palladium-catalyzed Heck-Mizoroki reactions in water in the absence of any organic co-solvent[J]. Tetrahedron 2009,65(34):7079-7084.
[7]Iranpoor N, Firouzabadi H, Tarassoli A, Fereidoonnezhad M.1,3,2,4-Diazadiphosphetidines as new P-N ligands for palladium-catalyzed Heck reaction in water[J]. Tetrahedron 2010,66 (13):2415-2421.
[8]Uozumi Y, Kimura T. Heck reaction in water with amphiphilic resin-supported palladium-phosphine complexes[J]. Synlett 2002,12:2045-2048.
[9]Pachon L D, Rothenberg G. Transition-metal nanoparticles:synthesis, stability and the leaching issue [J]. Appl. Organometal. Chem.,2008,22(6):288-299.
[10]Dizman B, Elasri M O, Mathias L J. Synthesis and antimicrobial activities of new water-soluble bis-quaternary ammonium methacrylate polymers [J]. J Appl Poly Sci.,2004, 94(2):635-642.
[11]Hsu M H, Hsu C M, Wang J C, et al. Air-stable Pd(Ⅱ) catalysts with cryptand-22 ligand for convenient and efficient Suzuki cross-coupling reactions [J]. Tetrahedron 2008,64(19): 4268-4274.
[12]Tsai F Y, Lin B N, Chen M J, et al. Anchored palladium bipyridyl complex in nanosized MCM-41:a recyclable and efficient catalyst for the Kumada-Corriu reaction [J]. Tetrahedron 2007,63(20):4304-4309.
[13]Huang W, Guo J P, Xiao Y J, et al. Palladium-benzimidazolium salt catalyst systems for Suzuki coupling:development of a practical and highly active palladium catalyst system for coupling of aromatic halides with arylboronic acids [J]. Tetrahedron 2005,61(41): 9783-9790.
[14]Nunez A, Sanchez A, Burgos C, et al. Synthesis of carbo-and heterobiaryls by intermolecular radical addition of aryl bromides onto aromatic solvents [J]. Tetrahedron 2004,60(29):6217-6224.
[15]Chen S N, Wu W Y, Tsai F Y. Hiyama reaction of aryl bromides with arylsiloxanes catalyzed by reusable palladium(II)/cationic bipyridyl system in water [J]. Tetrahedron 2008,64(35):8164-8168.
[16]Zeng M F, Du Y J, Shao L J, Qi C Z, Zhang X M. Palladium-catalyzed reductive homocoupling of aromatic halides and oxidation of alcohols[J]. J. Org. Chem.,2010,75(8): 2556-2563.
[17]Ma N, Zhu Z W, Wu Y J. Cyclopalladated ferrocenylimine:a highly effective catalyst for the borylation/Suzuki coupling reaction [J]. Tetrahedron 2007,63(22):4625-4629.
[1]Suzuki A. Cross-coupling reactions via organoboranes[J]. J. Organomet. Chem.,2002, 653(1-2):83-90.
[2]Stanforth S P. Catalytic cross-coupling reactions in biaryl synthesis[J]. Tetrahedron 1998, 54(3-4):263-303.
[3]Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds[J]. Chem. Rev.,1995,95(7):2457-2483.
[4]Uozumi Y, Nakai Y. An Amphiphilic resin-supported palladium catalyst for high-throughput cross-coupling in water[J]. Org. Lett.,2002,4(17):2997-3000.
[5]Zhang M C, Zhang W Q. Pd nanoparticles immobilized on pH-responsive and chelating nanospheres as an efficient and recyclable catalyst for Suzuki reaction in water[J]. J. Phys. Chem. C.,2008,112(16):6245-6252.
[6]Lyubimov S E, Korlyukov A A, Pisarev S A, Matveev V V, Chalykh A E, Zlotin S G, Davankov V A. Palladium-containing hypercrosslinked polystyrene as an easy to prepare catalyst for Suzuki reaction in water and organic solvents[J]. React. Funct. Polym.,2009,69 (10):755-758.
[7]Yi S S, Lee D H, Sin E Y, Lee Y S. Chitosan-supported palladium(0) catalyst for microwave-prompted Suzuki cross-coupling reaction in water[J]. Tetrahedron Lett.,2007,48 (38):6771-6775.
[8]Jiang N, Ragauskas A J. Environmentally friendly synthesis of biaryls:Suzuki reaction of aryl bromides in water at low catalyst loadings[J]. Tetrahedron Lett.,2006,47(2):197-200.
[9]Jin M J, Taher A, Kang H J, Choi M, Ryoo R. Palladium acetate immobilized in a hierarchicalMFI zeolite-supported ionic liquid:a highly active and recyclable catalyst for Suzuki reaction in water[J]. Green Chem.,2009, (11):309-313.
[10]Wei J F, Jiao J, Feng J J, Lv J, Zhang X R, Shi X Y, Chen Z G. PdEDTA held in an ionic liquid brush as a highly efficient and reusable catalyst for Suzuki reactions in water[J]. J. Org. Chem.,2009,74(16):6283-6286.
[11]Das D D, Sayari A. Applications of pore-expanded mesoporous silica 6. Novel synthesis of monodispersed supported palladium nanoparticles and their catalytic activity for Suzuki reaction[J]. J. Catal.,2007,246(1):60-65.
[12]Tzschucke C C, Andrushko V, Bannwarth W. Assessment of the reusability of Pd complexes supported on fluorous silica gel as catalysts for Suzuki couplings[J]. Eur. J. Org. Chem., 2005, (24):5248-5261.
[13]Wang L, Cai Chun. Fluorous silicagel-supported peruoro-tagged palladium nanoparticles catalyze Suzuki cross-coupling reaction in water[J]. J. Mol. Catal.A-Chem.,2009,306(1-2): 97-101.
[14]Sayah R.; Glegola K.; Framery E.; Dufaud V. Suzuki-Miyaura reactions of aryl chloride derivatives with arylboronic acids using mesoporous silica-supported aryl-dicyclohexylphosphine[J]. Adv. Synth. Catal.,2007,349(3):373-381.
[15]Karimi B, Elhamifar D, Clark J H, Hunt A J. Ordered mesoporous organosilica with ionic-liquid framework:An efficient and reusable support for the palladium-catalyzed Suzuki-Miyaura coupling reaction in water[J]. Chem. Eur. J.,2010,16(27):8047-8053.
[16]Liu J, Li Y Q, Zheng W J. Synthesis of immobilized nanopalladium on polymer-supported Schiff base, and study of its catalytic activity in the Suzuki-Miyaura reaction[J]. Monatsh Chem.,2009,140(12):1425-1429.
[17]Huang X J, Dong F, Chen L, Li Y Q. Nanopalladium immobilized on aminoethanol-functionalized poly(vinyl chloride):an easily prepared, air and moisture stable catalyst for Heck reactions[J]. Monatsh Chem.,2008,139(12):1447-1451.
[18]Schweizer S, Becht J M. Drian, C. L. Highly efficient reusable polymer-supported Pd catalysts of general use for the Suzuki reaction[J]. Tetrahedron 2010,66(3):765-772.
[19]Zhou W J, Wang K H, Wang J X, Gao Z R. Ligand-free, atom-efcient Suzuki-Miyaura type cross-coupling reactions at room temperature[J]. Tetrahedron 2010,66(38):7633-7641.