氮杂环卡宾钯化合物催化氯代芳烃胺化反应研究
|
摘要
本论文合成了一系列己知的的含有不同中性离去配体的氮杂环卡宾钯化合物,并考察了这些氮杂环卡宾钯化合物在芳基氯化物的催化胺化反应中的应用。主要工作如下：
一、氮杂环卡宾钯化合物的合成
根据文献合成方法,本论文合成了一系列含有不同中性离去配体的氮杂环卡宾钯化合物。试验方法如下所示：以苊醌1为原料与2,6-二异丙基苯胺反应合成得到亚胺化合物2,然后,亚胺化合物2与氯甲基甲醚反应得到咪唑盐3(Scheme1)；在K2C03作用下,咪唑盐3与PdCl2、吡啶及其衍生物进行反应,可以得到氮杂环卡宾钯化合物6a-c(Scheme2)。
其他氮杂环卡宾钯化合物6d-g须经氮杂环卡宾铜化合物作为转金属化试剂,从而形成氮杂环卡宾钯二聚体,然后解聚来制备(Scheme3)。
以上合成的氮杂环卡宾钯化合物6a-g均为已知化合物,本论文通过’HNMR、13CNMR对其进行了表征。
二、氮杂环卡宾钯化合物在氯代芳烃胺化反应中催化性能的研究
本论文研究了氮杂环卡宾钯化合物催化芳基氯化物的胺化反应(Scheme4)。分别对催化剂、碱和溶剂进行了筛选和优化。最后得到较优的反应条件为：氮气条件下,0.05mo1%的催化剂6d,1,4-二氧六环为溶剂,t-BuOK为碱,80℃下反应24h。
在此条件下,氮杂环卡宾钯化合物6d对一系列芳基、杂芳基氯化物与二级胺的偶联反应均取得了很好的催化效果,反应产率最高可达99%。
提高催化剂用量至0.5mo1%,氮杂环卡宾钯化合物6d对一系列芳基氯化物与一级胺的偶联反应也能得到很好的催化效果,反应产率最高可达99%。
In this thesis, some palladium NHC complexes with different neutral leaving group which had been reported were prepared. In addition, we investigated the catalytic ability of these complexes as precatalysts in the amination of aryl chlorides. The main resluts are shown as follows:
1. The synthesis of palladium NHC complexes
According to the methods of the literature, In this dissertation, we synthesized some palladium NHC complexes with different neutral leaving ligands which had been developed. The methods are shown as follows:the imine compound2prepared from acenaphthequinone1, then the Imine2reacted with the methoxy-(methyl)chloride to get IPr(BIAN) imidazolium chloride3(Scheme1). In the addition of K2CO3, the NHC-Pd complexes6a-c could be synthesized directly by imidazolium chloride3react with PdCl2and nitrogen-containing ligands, respectively (Scheme2).
The NHC-Pd complexes6d-g were prepared by the other methods. Firstly, we had to synthesize the NHC-Cu complexex as a transfer metal reagent by the imidazolium chloride3. Then we got the NHC-Pd dimers from the NHC-Cu complex. finally, we could got the NHC-Pd complexes6d-g through the dissociation of the NHC-Pd dimers(Scheme3).
All of these NHC-Pd complexes6a-g had been reported by Tu's group. In this dissertation, all of them were characterized by1H NMR、13C NMR.
Ⅱ. Studies on the catalytic ability of well-defined NHC-Pd complexes in the amination of aryl chloride
In this dissertation, the well-defind NHC-Pd complexes6a-g were regarded as precatalysts in the amination of aryl chloride(Scheme4). We screened and optimized the catalyst, base and solvent respectively. The optimal reaction conditions were: under anhydrous and anaerobic conditions, the loading of catalyst6d is0.05mol%, 1,4-dioxane as solvent, t-BuOK as base, reaction24h at80℃.
Under this conditions, the well-defind NHC-Pd complexex6d could effectively catalytic the coupling reaction of a series of (hetero)aryl chlorides with secondary amines, the yield could be up to99%.
Increasing the amount of catalyst to0.5mol%, the well-defind NHC-Pd complexex6d could effectively catalytic the coupling reaction of a series of aryl chlorides with primary amines. But it was failed to achieve good results for the heteroaryl chlorides.
一、氮杂环卡宾钯化合物的合成
根据文献合成方法,本论文合成了一系列含有不同中性离去配体的氮杂环卡宾钯化合物。试验方法如下所示：以苊醌1为原料与2,6-二异丙基苯胺反应合成得到亚胺化合物2,然后,亚胺化合物2与氯甲基甲醚反应得到咪唑盐3(Scheme1)；在K2C03作用下,咪唑盐3与PdCl2、吡啶及其衍生物进行反应,可以得到氮杂环卡宾钯化合物6a-c(Scheme2)。
其他氮杂环卡宾钯化合物6d-g须经氮杂环卡宾铜化合物作为转金属化试剂,从而形成氮杂环卡宾钯二聚体,然后解聚来制备(Scheme3)。
以上合成的氮杂环卡宾钯化合物6a-g均为已知化合物,本论文通过’HNMR、13CNMR对其进行了表征。
二、氮杂环卡宾钯化合物在氯代芳烃胺化反应中催化性能的研究
本论文研究了氮杂环卡宾钯化合物催化芳基氯化物的胺化反应(Scheme4)。分别对催化剂、碱和溶剂进行了筛选和优化。最后得到较优的反应条件为：氮气条件下,0.05mo1%的催化剂6d,1,4-二氧六环为溶剂,t-BuOK为碱,80℃下反应24h。
在此条件下,氮杂环卡宾钯化合物6d对一系列芳基、杂芳基氯化物与二级胺的偶联反应均取得了很好的催化效果,反应产率最高可达99%。
提高催化剂用量至0.5mo1%,氮杂环卡宾钯化合物6d对一系列芳基氯化物与一级胺的偶联反应也能得到很好的催化效果,反应产率最高可达99%。
In this thesis, some palladium NHC complexes with different neutral leaving group which had been reported were prepared. In addition, we investigated the catalytic ability of these complexes as precatalysts in the amination of aryl chlorides. The main resluts are shown as follows:
1. The synthesis of palladium NHC complexes
According to the methods of the literature, In this dissertation, we synthesized some palladium NHC complexes with different neutral leaving ligands which had been developed. The methods are shown as follows:the imine compound2prepared from acenaphthequinone1, then the Imine2reacted with the methoxy-(methyl)chloride to get IPr(BIAN) imidazolium chloride3(Scheme1). In the addition of K2CO3, the NHC-Pd complexes6a-c could be synthesized directly by imidazolium chloride3react with PdCl2and nitrogen-containing ligands, respectively (Scheme2).
The NHC-Pd complexes6d-g were prepared by the other methods. Firstly, we had to synthesize the NHC-Cu complexex as a transfer metal reagent by the imidazolium chloride3. Then we got the NHC-Pd dimers from the NHC-Cu complex. finally, we could got the NHC-Pd complexes6d-g through the dissociation of the NHC-Pd dimers(Scheme3).
All of these NHC-Pd complexes6a-g had been reported by Tu's group. In this dissertation, all of them were characterized by1H NMR、13C NMR.
Ⅱ. Studies on the catalytic ability of well-defined NHC-Pd complexes in the amination of aryl chloride
In this dissertation, the well-defind NHC-Pd complexes6a-g were regarded as precatalysts in the amination of aryl chloride(Scheme4). We screened and optimized the catalyst, base and solvent respectively. The optimal reaction conditions were: under anhydrous and anaerobic conditions, the loading of catalyst6d is0.05mol%, 1,4-dioxane as solvent, t-BuOK as base, reaction24h at80℃.
Under this conditions, the well-defind NHC-Pd complexex6d could effectively catalytic the coupling reaction of a series of (hetero)aryl chlorides with secondary amines, the yield could be up to99%.
Increasing the amount of catalyst to0.5mol%, the well-defind NHC-Pd complexex6d could effectively catalytic the coupling reaction of a series of aryl chlorides with primary amines. But it was failed to achieve good results for the heteroaryl chlorides.
引文
[1]Doering, W. V. E., Hoffmann, A, K. The Addition of Dichloro carbene to Olefins. [J] J Am Chem Soc,1954,76(23):6162-6265
[2]Skell, P. S., Sandier, S. Reations of 1,1—Dihalocyclopropanes with Electrophlic Reagents: Synthetic Rome for Inserting a Carbon Atom between the Atoms of a Double Bond. [J] J Am Chem Soc,1958,80(8):2024-2025
[3]Fischer, E. O., Maasbol, A. On the Existence of a Tungsten Carbonyl Carbene Complex [J] Angew Chem Int Ed,1964,3(8):580-581
[4]H-W Wanzlick, H,-J Schfnherr. Direct Synthesis Of a Mercury Salt-Carbene Complex [J] Angew Chem Int Ed,1968,7(2):141-142
[5]Ofele, K.1,3-Dimethyl-4-imidazolinyliden-(2)-pentacarbonylchrom ein neuer ubergangsm-etall-carben-komplex. [J]J. Organomet Chem,1968,12,42.
[6]Anthony J Arduengo Ⅲ. Richard L Harlow, Michael Kline, A Stable crystalline carbene. [J] J.Am Chem Soc,1991,113(1):361-363
[7]W. A. Herrmann; M. Elison. Metal Complexes of N-Heterocyclic Carbenes—A New Structural Principle for Catalysts in Homogeneous Catalysis. [J] Angew. Chem., Int. Ed.1995, 107,2602-2605.
[8](a)Bohm, V. P. Wj; Herrmann, W. A. The "Wanzlick Equilibrium". [J] Angew. Chem. Int. Ed.2000,39,4036. (b) Herrmann, W.A.; Kocher, C. N-Heterocyclic Carbenes. [J] Angew. Chem. Int. Ed.1997,36,2162. (c)Herrmann, W. A.; Weskamp, T. Metal complexes of stable carbenes. [J] Adv. Organomet. Chem.2001,48,1.
[9]Chunming Zhang, Mark L. Trudell, Steven P. Nolan. Palladium-Imidazol-2-ylidene Complexes as Catalysts for Facile and Efficient Suzuki Cross-Coupling Reactions of Aryl Chlorides with Arylboronic Acids. [J] J. Org. Chem.1999,64,3804-3805
[10]Tina M. Trnka and Robert H. Grubbs. The Development of L2X2Ru=CHR Olefin Metathesis Catalysts:□ An Organometallic Success Story. [J] Acc. Chem. Res.,2001,34 (1), 18-29
[11]Bourissou, D., Bertrand, G. Stable Carbenes. [J] Chem. Rev.2000,100,39.
[12]Scarborough C. C.,Grady M. J. W. Heterocyclic Carbenes. [J] Angew. Chem. Int. Ed.2005,44,25.
[13]A. J. Arduengo. Preparationofl,3-Disubstituted ImidazoliumSalts. [P] United States Patent, 1991,5077414.
[14]Arduengo, A. J., Krafczyk R. Imidazolylidenes, Imidazolinylidenes and Imi-dazolidines. [J] Tetrahedron.1999,55,14523-14534.
[15]Jafapour L., Steven E. D. A sterically demanding nucleophilic carbene:1,3-bis(2,6-diisopr-opylphenyl)imidazol-2-ylidene). Thermochemistry and catalytic application in olefin metathesis. [J] J. Organoment. Chem.2000,606,49-54.
[16]Delaude L., Szypa M. New In situ Generated Ruthenium Catalysts Bearing N-Heterocyclic Carbene Ligands for the Ring-Opening Metathesis Polymerization of Cyclooctene. [J] Adv. Synth. Catal.2002,344,749-756.
[17]Arduengo A. J., Goerlich J. R., Marshall W. J. A stable diaminocarbene. [J] J. Am. Chem. Soc.1995,117 (44),11027-11028
[18]Hadei, N., Kantchev, E. A. B., Organ. M. G. Room-Temperature Negishi Cross-Coupling of Unactivated Alkyl Bromides with Alkyl Organozinc Reagents Utilizing a Pd/N-Heterocyclic Carbene Catalyst. [J] J. Org. Chem,2005,70,8503.
[19]Herrmann, W. A., K&her, C. N-Heterocyclic Carbenes. [J] Angew. Chem. Int. Ed. Engl. 1997,36,2162
[20]Weskamp, T., B&m, V. P.W., Herrmann, W. A., Combining N-heterocyclic carbenes and phosphines:improved palladium(Ⅱ) catalysts for aryl coupling reactions. [J] J. Organomet. Chem.1999,585,348
[22]Douthwaite, R. E., Silcock, P. J., Green, M. L. H. Cationic Nickel(II) Complexes of Chelating N-Heterocyclic Carbenes. [J] Organometallics.1999,18,4584
[22]Herrmann, W. A., Schwarz, J., High-Yield Syntheses of Sterically Demanding Bis(N-hetero-cyclic carbene) Complexes of Palladium. [J] Organometallics.1999,18,4082
[23]Xinjun, L., Costabile, C., Dorta, R. Identification and Characterization of a New Family of Catalytically Highly Active Imidazolin-2-ylidenes. [J] J. Am. Chem. Soc.2008,130,6848-6858
[24]Wanzhi, C., Bo, L., Na, Z. Synthesis of Metal N-Heterocyclic Carbene Complexes. [J] Progress In Chemistry.2010,22(11),2134-2146.
[25]Liu, L., Wang, F,. Shi, M. Synthesis of Chiral Bis(N-heterocyclic carbene) Palladium and Rhodium Complexes with 1,1'-Biphenyl Scaffold and Their Application in Asymmetric Catalysis. [J] Organometallics.,2009,28,4416-4420
[26]Yong K., Binyuan L., Baiquan, W. Synthesis, Structures, and Norbornene Polymerization Behavior of Bis(aryloxide-N-heterocyclic carbene) Palladium Complexes. [J] Organometallics> 2009,28:5934—5940
[27]Harrison, M. J. W., Ivan, J. B. L. Facile Synthesis of Silver(I)-Carbene Complexes. Useful Carbene Transfer Agents. [J] Organometallics,1998,17 (5),972-975
[28]Kalyan V. Vasudevan, Rachel R. Butorac, Colin D. Abernethy and Alan H. Cowley*. Synthesis and coordination compounds of a bis(imino)acenaphthene(BIAN)-supported N-heterocyclic carbene. [J] Dalton Trans.,2010,39,7401-7408
[29]Cardin D. J, Cetinkay B, Lappert M. F, et al. An electron-rich olefin as a source of co-ordinated carbene; synthesis of trans-PtCl2[C(NPhCH2)2]PEt3. [J] J. Chem. Soc. D.,1971, 400—401
[29]Wanzhi, C, Bo, L., Na, Z. Synthesis of Metal N-Heterocyclic Carbene Complexes. [J] Progress In Chemistry.2010,22(11),2134-2146.
[30]Viciano M, Poyatos M, Lledos A. et al. C-H Oxidative Addition of Bisimidazolium Salts to Iridium and Rhodium Complexes, and N-Heterocyclic Carbene Generation. A Combined Experimental and Theoretical Study. [J] Organometallics,2006.25:1120—1134
[31]Bo Liu, Bin Liu, and Wanzhi Chen. et al. Copper(II) Hydroxide Complexes of N-Heterocyclic Carbenes and Catalytic Oxidative Amination of Arylboronic Acids. [J] Organometallics,2010,29:1457—1464
[32]Helgard G. Raubenheimer, Stephanie Cronje. Carbene complexes derived from lithiated heterocycles, mainly azoles, by transmetallation. [J] J. Organomet. Chem.,2001,617: 170—181
[33]Jiang, Lan, Zhao, Defeng, Li, Zhengning*. Progress in the Heck Reaction and Suzuki Reaction Catalyzed by Pd-N-Heterocyclic Carbene Complexes. [J] Chinese Journal of Organic Chemistry.2010,30(2),200-210
[34]Wolfgang A. Herrmann, Claus-Peter Reisinger, Michael Spiegler. ChelatingN-Heterocyclic Carbene Ligands in Palladium-Catalyzed Heck-Type Reactions [J] J. Organomet. Chem,1998, 557(1),93-96.
[35]Christian W. K. Gstottmayr, Volker P. W. Bohm, Wolfgang A. Herrmann, et al. A Defined N-Heterocyclic Carbene Complex for the Palladium-Catalyzed Suzuki Cross-Coupling of Aryl Chlorides at Ambient Temperatures.]J] Angew. Chem., Int. Ed.,2002,41,1363-1365.
[36]Christopher J. O'Brien. Eric Assen B. Kantchev., Michael G. Organ, et al. Easily Prepared Air-and Moisture-Stable Pd-NHC (NHC=N-Heterocyclic Carbene) Complexes:A Reliable, User-Friendly, Highly Active Palladium Precatalyst for the Suzuki-Miyaura Reaction. [J] Chemistry-A European Journal.2006,12,4743-4748.
[37]Tao Tu,* Zheming Sun, Weiwei Fang, et al. Robust Acenaphthoimidazolylidene Palladium Complexes:Highly Efficient Catalysts for Suzuki Miyaura Couplings with Sterically Hindered Substrates. [J] Org. Lett.2012,14,4250-4253
[38]D. Milstein, J. K. Stille. A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compoundscatalyzed bypalladium. [J] J. Am. Chem. Soc.,1978, 100(11).3636-3638.
[39]J. K. Stille. The Palladium-catalyzed cross-coupling reactions of organotinreagents with organic electrophiles. [J] Angew. Chem. Int. Ed.1986,25.508-524.
[40]Thomas Weskamp, Volker P.W Bohm, Wolfgang. A.Herrmann. Combining N-heterocyclic carbenes and phosphines:improved palladium(Ⅱ) catalysts for aryl coupling reactions. [J] J. Organomet. Chem.1999,585,348—352
[41]T. Hiyama. Yasuo Hatanaka. Palladium—catalyzed cross-coupling reaction of organo metalloids through activation with fluoride ion, [J]Pure Appl Chem.,1994,66(7):1471-1478.
[42]Tamejiro Hiyama, How I came across the silicon-based cross-coupling reaction. [J] J.Organomet. Chem.2002,653,58-61.
[43]Scott. E. Denmark. John D. Baird. Palladium-Catalyzed Cross-Coupling Reactions of Silanolates:A Paradigm Shift in Silicon-Based Cross-Coupling Reactions. [J] Chem. Eur. J. 2006,12,4954-4963.
[44]Yoshiaki Nakao,Tamejiro Hiyama, Silicon-based cross-coupling reaction:an environmen-tally benign version. [J] Chem. Soc. Rev.2011,40,4893-4901.
[45]Xiaoming Zhang, Qinqin Xia, Wanzhi Chen. Synthesis of tetra-and pentacoordinate palladium complexes of functionalized N-heterocyclic carbenes and a comparative study of their catalytic activities. [J] Dalton Trans.,2009,7045-7054.
[46]Zheng-Song Gu, Li-Xiong Shao, Jian-Mei Lu. NHC-Pd(II)-Im (NHC= N-heterocyclic carbene; Im= 1-methylimidazole)complex catalyzed Hiyama reaction of aryl chlorides with aryltrime thoxysilanes. [J] J.Organomet. Chem.2012,700,132-134
[47]Kohei Tamao, Koji Sumitani, Makoto Kumada. Selective carbon-carbon bond formation by cross-coupling of Grignard reagents with organic halides. Catalysis by nickel-phosphine complexes. [J] J. Am. Chem. Soc.,1972,94,4374-4376.
[48]Masaaki Yamamura, Ichiro Moritani, Shun-Ichi Murahashi. The reaction of σ-vinylpalladium complexes with alkyllithiums. Stereospecific syntheses of olefins from vinyl halides and alkyllithiums. [J] J. Organomet.Chem.,1975,91, C39-C42.
[49]Jinkun Huang, Steven P. Nolan, Efficient Cross-Coupling of Aryl Chlorides with Aryl Grignard Reagents (Kumada Reaction) Mediated by a Palladium/Imidazolium Chloride System. [J] J. Am. Chem. Soc.,1999,121,9889-9890.
[50]Caroline E. Hartmann, Steven P. Nolan, Catherine S. J. Cazin, Highly Active [Pd(μ-Cl)(Cl)(NHC)]2 (NHC= N-Heterocyclic Carbene) in the Cross-Coupling of Grignard Reagents with Aryl Chlorides. [J] Organometallics,2009,28,2915-2919.
[51]Joanna Nasielski, Nilofaur Hadei, Michael G. Organ, et al. Structure-Activity Relationship Analysis of Pd-PEPPSI Complexes in Cross-Couplings:A Close Inspection of the Catalytic Cycle and the Precatalyst Activation Model. [J] Chemistry-A European Journal. 2010,12,10844-10853
[52]C. Valente, M. E. Belowich, M. G. Organ, et al. Pd-PEPPSI Complexes and the Negishi Reaction. [J] Eur. J. Org. Chem,2010,23,4343-4354.
[53]George T. Achonduh, Niloufar Hadei, Michael G. Organ, et al. On the role of additives in alkyl-alkyl Negishi cross-couplings. [J] Chem. Commun,2010,46,4109—4111
[54]Wolfgang A. Herrmann, Martina Elison, Georg R. J. Artus. et al. Metal Complexes of N-Heterocyclic Carbenes—A New Structural Principle for Catalysts in Homogeneous Catalysis.[J] Angewandte Chemie International Edition in English.1995,34(21),2371-22374
[55]Guang-Rong Peh, Eric Assen B. Kantchev, Jackie Y. Ying. et al. N-heterocycle carbene (NHC)-ligated cyclopalladated N,N-dimethylbenzylamine:a highly active, practical and versatile catalyst for the Heck-Mizoroki reaction. [J] Org. Biomol. Chem,2009,7,2110-2119
[56]Ming-Tao Ma, Jian-Mei Lu. Dinuclear Pd(II)-NHC complex derived from proline and its application toward Mizoroki-Heck reaction performed in water. [J] Appl. Organometal. Chem. 2012,26,175-179
[57]Ting-Ting Gao, Ai-Ping Jin and Li-Xiong Shao. N-Heterocyclic carbene-palladium(Ⅱ)-1-methyl-imidazole complex catalyzed Mizoroki-Heck reaction of aryl chlorides with styrenes. [J] Beilstein J. Org. Chem.2012,8,1916-1919.
[58]S. Caddick, F. G. N. Cloke, M. R. V. Williams, et al. An improved synthesis of bis(1,3-di-N-tert-butylimidazol-2-ylidene)palladium(0) and its use in C-C and C-N coupling reactions [J]J. Organomet. Chem.,2001,617-618,635-639.
[59]Manoja K. Samantaray, Mobin M. Shaikh, Prasenjit Ghosh. Copper-free and amine-free Sonogashira coupling in air in a mixed aqueous medium by palladium complexes of N/O-functionalized N-heterocyclic carbenes. [J] J. Organomet. Chem.,2001,617-618,635-639.
[60]Fen-Tair Luo, Hung-Kun Lo. Short synthesis of bis-NHC-Pd catalyst derived from caffeine and its applicationsto Suzuki, Heck, and Sonogashira reactions in aqueous solution. [J] J. Organomet. Chem.,2011,696,1262-1265.
[61]Anthony Chartoire, Xavier Frogneux, Steven P. Nolan, et al. [Pd(IPr*)(3-Cl-pyridinyl)Cl2]: A Novel and Efficient PEPPSI Precatalyst. [J] Organometallics.2012,31,6947-6951
[62]Anthony Chartoire, Xavier Frogneux, Steven P. Nolan. An Efficient Palladium-NHC (NHC = N-Heterocyclic Carbene) and Aryl Amination Pre-Catalyst:[Pd (IPr*) (cinnamyl)Cl]. [J] Adv. Synth. Catal.2012,354,1897-1901
[63]Anthony Chartoire, Arnaud Boreux, Steven P. Nolan, et al. Solvent-free aryl amination catalysed by [Pd(NHC)]complexes. [J] RSC Adv.,2013,3,3840-3843
[64]Michael G. Organ, Mirvat Abdel-Hadi, Stephanie Avola. et al. Pd-Catalyzed Aryl AminationMediated by Well Defined, N-HeterocyclicCarbene (NHC)-PdPrecatalysts, PEPPSI. [J] Chem. Eur. J.2008,14,2443-2452
[65]Ka Hou Hoi, Jennifer A. Coggan, Michael G. Organ. Pd-PEPPSI-IPentcl:An Effective Catalyst for the Preparation of Triarylamines. [J] Chem. Eur. J.2013,19,843-845
[66]Tao Tu, Weiwei Fang, Jian Jiang. A highly efficient precatalyst for amination of aryl chlorides:synthesis,structure and application of a robust a cenaphthoimidazolyli-dene palladium complex. [J] Chem. Commun.,2011,47, 12358-12360
[67]Lei Zhu, Ting-Ting Gao, Li-Xiong Shao. Well-defined NHCePd(Ⅱ)eIm (NHC= N-heterocyclic carbene; Im= 1-methylimidazole) complexes catalyzed amination of aryl chlorides. [J] Tetrahedron,2011,67,5150-5155.
[68]Wen-Xin Chen, Li-Xiong Shao. N-Heterocyclic Carbene-Palladium(Ⅱ)-1-Methyl-imidazole Complex Catalyzed Amination between Aryl Chlorides and Amides. [J] J. Org. Chem. 2012,77,9236-9239
[69]S. Suwanprasop, T. Nhujak, S. Roengsumran, A. Petsom, Petroleum Marker Dyes Synthesized from Cardanol and Aniline Derivatives. [J] Ind. Eng. Chem. Res.,2004,43, 4973-4978
[70]Xiaowei Hao, Jia Yuan, Sheng-Hua Liu. et al. Air-stable and highly efficient indenyl-derived phosphine ligand:Application to Buchwald eHartwig amination reactions. [J] Journal of Organo metallic Chemistry.2012,706-707,99-105.
[71]Xusheng Shao, Philip W. Lee, Xuhong Qian. et al. cis-Configuration:A New Tactic/Rationale for Neonicotinoid Molecular Design. [J] J. Agric. Food Chem.,2011,59 (7), 2943-2949
[72]Wenmu Li, Shenghai Li, Suobo Zhang, et al. Synthesis of Bis(amine anhydride)s for Novel High Tgs and Organosoluble Poly(amine imide)s by Palladium-Catalyzed Amination of 4-Chlorophthalide Anhydride. [J] Macromolecules,2007,40 (23),8205-8211
[73]S. A. Lawrence, Amines:Synthesis,Properties and Application. [M] CambridgeUniversity Press, Cambridge,2004;
[74]M. B. Smith, J. March. March's Advanced Organic Chemistry:Reactions, Mechanisms and Structure. [M] John Wiley & Sons Inc.,New Y ork,5th e dn,2001;
[75]H.Heaney. The Benzyne and Related Intermediates. [J] Chem. Rev.,1962,62,81.
[76]J. F. Hartwig, E. I. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis. [M] Wiley-Interscience, New York,2002;
[77]J. F. Hartwig, A. Ricci, Modern Amination Methods. [M] Wiley-VCH, Weinheim,2000.
[78]Masanori Kosugil, Masayuki Kameyama, Toshihiko Migita. Palladium-catalyzed aromatic amination of aryl bromides with N,N-di-ethylamino-tributylin. [J] T. Chem. Lett.1983,927
[79]Anil S. Guram, Roger A. Rennels, Stephen L. Buchwald. A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines. [J] An gew. Chem. Int. Ed.1995,34(12). 1348-1350.
[80]Janis Louie, John F. Hartwig. Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents. [J] Tetrahedron. Lett.1995, 36(21),3609-3612
[81]John F. Hartwig. Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates:Scope and Mechanism. [J] Angew. Chem. Int. Ed.1998, 37(15).2046-2067.
[82]David S. Surry, Stephen L. Buchwald. Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide. [J] Chem. Sci.,2011,2,27-50.
[83]Sebastien Meiries, Klaus Speck, Steven P. Nolan, et al. [Pd(IPr*OMe)(acac)Cl]:Tuning the N-Heterocyclic Carbene in Catalytic C-N Bond Formation. [J] Organometallics.2013,32,330-339
[84]Sebastien Meiries, Anthony Chartoire, Steven P. Nolan, et al. [Pd(IPr*)(acac)Cl]:An Easily Synthesized, Bulky Precatalyst for C-NBond Formation. [J] Organometallics.2012,31,3402-3409
[85]Weiwei Fang, Jian Jiang, Tao Tu. et al. Novel robust benzimidaz olylidene palladium complexes:synthesis structure, and catalytic applications in aminati on of chloroarenes. [J] Tetrahedron.2013,69,673-679.
[86]Stephanie Ho, Ganna Bondarenko, Arturo Orellana. et al. Synthesis of Acyl Pyrroles via Palladium-Catalyzed Carbonylative Amination of Aryl and Alkenyl Iodides. [J] J. Org. Chem. 2012,77,2008-2012
[87]Sarim Dastgir,*Karl S. Coleman, Malcolm L. H. Green*, et al. Synthesis, Structure, and Temperature-Dependent Dynamics of Neutral Palladium Allyl Complexes of Annulated Diaminocarbenes and Their Catalytic Application for C-C and C-N Bond Formation Reactions. [J] Organometallics.2010,29,4858-4870.
[88]Kalyan V. Vasudevan, Rachel R. Butorac, Alan H. Cowley*. et al. Synthesis and coordination compounds of a bis(imino)acenaphthene (BI AN)-supported N-heterocyclic carbene. [J] Dalton Trans.,2010,39,7401-7408.
[89]Christopher J. O4Brien, Eric Assen B. Kantchev, Michael G. Organ*, et al. Easily Prepared Air-and Moisture-Stable Pd-NHC (NHC= N-Heterocyclic Carbene) Complexes:A Reliable, User-Friendly, Highly Active PalladiumPrecatalyst for the Suzuki-Miyaura Reaction. [J] Chem. Eur. J.2006,12,4743-4748
[90]Cecilia A. Citadelle, Erwan Le Nouy, Catherine S. J. Cazin. et al. Simple and versatile synthesis of copper and silver N-heterocyclic carbene complexes in water or organic solvents. [J] Dalton Trans.,2010,39,4489-4491
[91]Marc R. L. Furst and Catherine S. J. Cazin. Copper N-heterocyclic carbene (NHC) complexes as carbene transfer reagents. [J] Chem. Commun.,2010,46,6924-6925
[92]Ming-Tsz Chen, David A. Vicic, Oscar Navarro*. et al. (N-Heterocyclic Carbene) PdCl2(TEA) Complexes:Studies on the Effect of the "Throw-Away" Ligand in Catalytic Activity. [J] Organometallics,2011,30 (18),5052-5056
[2]Skell, P. S., Sandier, S. Reations of 1,1—Dihalocyclopropanes with Electrophlic Reagents: Synthetic Rome for Inserting a Carbon Atom between the Atoms of a Double Bond. [J] J Am Chem Soc,1958,80(8):2024-2025
[3]Fischer, E. O., Maasbol, A. On the Existence of a Tungsten Carbonyl Carbene Complex [J] Angew Chem Int Ed,1964,3(8):580-581
[4]H-W Wanzlick, H,-J Schfnherr. Direct Synthesis Of a Mercury Salt-Carbene Complex [J] Angew Chem Int Ed,1968,7(2):141-142
[5]Ofele, K.1,3-Dimethyl-4-imidazolinyliden-(2)-pentacarbonylchrom ein neuer ubergangsm-etall-carben-komplex. [J]J. Organomet Chem,1968,12,42.
[6]Anthony J Arduengo Ⅲ. Richard L Harlow, Michael Kline, A Stable crystalline carbene. [J] J.Am Chem Soc,1991,113(1):361-363
[7]W. A. Herrmann; M. Elison. Metal Complexes of N-Heterocyclic Carbenes—A New Structural Principle for Catalysts in Homogeneous Catalysis. [J] Angew. Chem., Int. Ed.1995, 107,2602-2605.
[8](a)Bohm, V. P. Wj; Herrmann, W. A. The "Wanzlick Equilibrium". [J] Angew. Chem. Int. Ed.2000,39,4036. (b) Herrmann, W.A.; Kocher, C. N-Heterocyclic Carbenes. [J] Angew. Chem. Int. Ed.1997,36,2162. (c)Herrmann, W. A.; Weskamp, T. Metal complexes of stable carbenes. [J] Adv. Organomet. Chem.2001,48,1.
[9]Chunming Zhang, Mark L. Trudell, Steven P. Nolan. Palladium-Imidazol-2-ylidene Complexes as Catalysts for Facile and Efficient Suzuki Cross-Coupling Reactions of Aryl Chlorides with Arylboronic Acids. [J] J. Org. Chem.1999,64,3804-3805
[10]Tina M. Trnka and Robert H. Grubbs. The Development of L2X2Ru=CHR Olefin Metathesis Catalysts:□ An Organometallic Success Story. [J] Acc. Chem. Res.,2001,34 (1), 18-29
[11]Bourissou, D., Bertrand, G. Stable Carbenes. [J] Chem. Rev.2000,100,39.
[12]Scarborough C. C.,Grady M. J. W. Heterocyclic Carbenes. [J] Angew. Chem. Int. Ed.2005,44,25.
[13]A. J. Arduengo. Preparationofl,3-Disubstituted ImidazoliumSalts. [P] United States Patent, 1991,5077414.
[14]Arduengo, A. J., Krafczyk R. Imidazolylidenes, Imidazolinylidenes and Imi-dazolidines. [J] Tetrahedron.1999,55,14523-14534.
[15]Jafapour L., Steven E. D. A sterically demanding nucleophilic carbene:1,3-bis(2,6-diisopr-opylphenyl)imidazol-2-ylidene). Thermochemistry and catalytic application in olefin metathesis. [J] J. Organoment. Chem.2000,606,49-54.
[16]Delaude L., Szypa M. New In situ Generated Ruthenium Catalysts Bearing N-Heterocyclic Carbene Ligands for the Ring-Opening Metathesis Polymerization of Cyclooctene. [J] Adv. Synth. Catal.2002,344,749-756.
[17]Arduengo A. J., Goerlich J. R., Marshall W. J. A stable diaminocarbene. [J] J. Am. Chem. Soc.1995,117 (44),11027-11028
[18]Hadei, N., Kantchev, E. A. B., Organ. M. G. Room-Temperature Negishi Cross-Coupling of Unactivated Alkyl Bromides with Alkyl Organozinc Reagents Utilizing a Pd/N-Heterocyclic Carbene Catalyst. [J] J. Org. Chem,2005,70,8503.
[19]Herrmann, W. A., K&her, C. N-Heterocyclic Carbenes. [J] Angew. Chem. Int. Ed. Engl. 1997,36,2162
[20]Weskamp, T., B&m, V. P.W., Herrmann, W. A., Combining N-heterocyclic carbenes and phosphines:improved palladium(Ⅱ) catalysts for aryl coupling reactions. [J] J. Organomet. Chem.1999,585,348
[22]Douthwaite, R. E., Silcock, P. J., Green, M. L. H. Cationic Nickel(II) Complexes of Chelating N-Heterocyclic Carbenes. [J] Organometallics.1999,18,4584
[22]Herrmann, W. A., Schwarz, J., High-Yield Syntheses of Sterically Demanding Bis(N-hetero-cyclic carbene) Complexes of Palladium. [J] Organometallics.1999,18,4082
[23]Xinjun, L., Costabile, C., Dorta, R. Identification and Characterization of a New Family of Catalytically Highly Active Imidazolin-2-ylidenes. [J] J. Am. Chem. Soc.2008,130,6848-6858
[24]Wanzhi, C., Bo, L., Na, Z. Synthesis of Metal N-Heterocyclic Carbene Complexes. [J] Progress In Chemistry.2010,22(11),2134-2146.
[25]Liu, L., Wang, F,. Shi, M. Synthesis of Chiral Bis(N-heterocyclic carbene) Palladium and Rhodium Complexes with 1,1'-Biphenyl Scaffold and Their Application in Asymmetric Catalysis. [J] Organometallics.,2009,28,4416-4420
[26]Yong K., Binyuan L., Baiquan, W. Synthesis, Structures, and Norbornene Polymerization Behavior of Bis(aryloxide-N-heterocyclic carbene) Palladium Complexes. [J] Organometallics> 2009,28:5934—5940
[27]Harrison, M. J. W., Ivan, J. B. L. Facile Synthesis of Silver(I)-Carbene Complexes. Useful Carbene Transfer Agents. [J] Organometallics,1998,17 (5),972-975
[28]Kalyan V. Vasudevan, Rachel R. Butorac, Colin D. Abernethy and Alan H. Cowley*. Synthesis and coordination compounds of a bis(imino)acenaphthene(BIAN)-supported N-heterocyclic carbene. [J] Dalton Trans.,2010,39,7401-7408
[29]Cardin D. J, Cetinkay B, Lappert M. F, et al. An electron-rich olefin as a source of co-ordinated carbene; synthesis of trans-PtCl2[C(NPhCH2)2]PEt3. [J] J. Chem. Soc. D.,1971, 400—401
[29]Wanzhi, C, Bo, L., Na, Z. Synthesis of Metal N-Heterocyclic Carbene Complexes. [J] Progress In Chemistry.2010,22(11),2134-2146.
[30]Viciano M, Poyatos M, Lledos A. et al. C-H Oxidative Addition of Bisimidazolium Salts to Iridium and Rhodium Complexes, and N-Heterocyclic Carbene Generation. A Combined Experimental and Theoretical Study. [J] Organometallics,2006.25:1120—1134
[31]Bo Liu, Bin Liu, and Wanzhi Chen. et al. Copper(II) Hydroxide Complexes of N-Heterocyclic Carbenes and Catalytic Oxidative Amination of Arylboronic Acids. [J] Organometallics,2010,29:1457—1464
[32]Helgard G. Raubenheimer, Stephanie Cronje. Carbene complexes derived from lithiated heterocycles, mainly azoles, by transmetallation. [J] J. Organomet. Chem.,2001,617: 170—181
[33]Jiang, Lan, Zhao, Defeng, Li, Zhengning*. Progress in the Heck Reaction and Suzuki Reaction Catalyzed by Pd-N-Heterocyclic Carbene Complexes. [J] Chinese Journal of Organic Chemistry.2010,30(2),200-210
[34]Wolfgang A. Herrmann, Claus-Peter Reisinger, Michael Spiegler. ChelatingN-Heterocyclic Carbene Ligands in Palladium-Catalyzed Heck-Type Reactions [J] J. Organomet. Chem,1998, 557(1),93-96.
[35]Christian W. K. Gstottmayr, Volker P. W. Bohm, Wolfgang A. Herrmann, et al. A Defined N-Heterocyclic Carbene Complex for the Palladium-Catalyzed Suzuki Cross-Coupling of Aryl Chlorides at Ambient Temperatures.]J] Angew. Chem., Int. Ed.,2002,41,1363-1365.
[36]Christopher J. O'Brien. Eric Assen B. Kantchev., Michael G. Organ, et al. Easily Prepared Air-and Moisture-Stable Pd-NHC (NHC=N-Heterocyclic Carbene) Complexes:A Reliable, User-Friendly, Highly Active Palladium Precatalyst for the Suzuki-Miyaura Reaction. [J] Chemistry-A European Journal.2006,12,4743-4748.
[37]Tao Tu,* Zheming Sun, Weiwei Fang, et al. Robust Acenaphthoimidazolylidene Palladium Complexes:Highly Efficient Catalysts for Suzuki Miyaura Couplings with Sterically Hindered Substrates. [J] Org. Lett.2012,14,4250-4253
[38]D. Milstein, J. K. Stille. A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compoundscatalyzed bypalladium. [J] J. Am. Chem. Soc.,1978, 100(11).3636-3638.
[39]J. K. Stille. The Palladium-catalyzed cross-coupling reactions of organotinreagents with organic electrophiles. [J] Angew. Chem. Int. Ed.1986,25.508-524.
[40]Thomas Weskamp, Volker P.W Bohm, Wolfgang. A.Herrmann. Combining N-heterocyclic carbenes and phosphines:improved palladium(Ⅱ) catalysts for aryl coupling reactions. [J] J. Organomet. Chem.1999,585,348—352
[41]T. Hiyama. Yasuo Hatanaka. Palladium—catalyzed cross-coupling reaction of organo metalloids through activation with fluoride ion, [J]Pure Appl Chem.,1994,66(7):1471-1478.
[42]Tamejiro Hiyama, How I came across the silicon-based cross-coupling reaction. [J] J.Organomet. Chem.2002,653,58-61.
[43]Scott. E. Denmark. John D. Baird. Palladium-Catalyzed Cross-Coupling Reactions of Silanolates:A Paradigm Shift in Silicon-Based Cross-Coupling Reactions. [J] Chem. Eur. J. 2006,12,4954-4963.
[44]Yoshiaki Nakao,Tamejiro Hiyama, Silicon-based cross-coupling reaction:an environmen-tally benign version. [J] Chem. Soc. Rev.2011,40,4893-4901.
[45]Xiaoming Zhang, Qinqin Xia, Wanzhi Chen. Synthesis of tetra-and pentacoordinate palladium complexes of functionalized N-heterocyclic carbenes and a comparative study of their catalytic activities. [J] Dalton Trans.,2009,7045-7054.
[46]Zheng-Song Gu, Li-Xiong Shao, Jian-Mei Lu. NHC-Pd(II)-Im (NHC= N-heterocyclic carbene; Im= 1-methylimidazole)complex catalyzed Hiyama reaction of aryl chlorides with aryltrime thoxysilanes. [J] J.Organomet. Chem.2012,700,132-134
[47]Kohei Tamao, Koji Sumitani, Makoto Kumada. Selective carbon-carbon bond formation by cross-coupling of Grignard reagents with organic halides. Catalysis by nickel-phosphine complexes. [J] J. Am. Chem. Soc.,1972,94,4374-4376.
[48]Masaaki Yamamura, Ichiro Moritani, Shun-Ichi Murahashi. The reaction of σ-vinylpalladium complexes with alkyllithiums. Stereospecific syntheses of olefins from vinyl halides and alkyllithiums. [J] J. Organomet.Chem.,1975,91, C39-C42.
[49]Jinkun Huang, Steven P. Nolan, Efficient Cross-Coupling of Aryl Chlorides with Aryl Grignard Reagents (Kumada Reaction) Mediated by a Palladium/Imidazolium Chloride System. [J] J. Am. Chem. Soc.,1999,121,9889-9890.
[50]Caroline E. Hartmann, Steven P. Nolan, Catherine S. J. Cazin, Highly Active [Pd(μ-Cl)(Cl)(NHC)]2 (NHC= N-Heterocyclic Carbene) in the Cross-Coupling of Grignard Reagents with Aryl Chlorides. [J] Organometallics,2009,28,2915-2919.
[51]Joanna Nasielski, Nilofaur Hadei, Michael G. Organ, et al. Structure-Activity Relationship Analysis of Pd-PEPPSI Complexes in Cross-Couplings:A Close Inspection of the Catalytic Cycle and the Precatalyst Activation Model. [J] Chemistry-A European Journal. 2010,12,10844-10853
[52]C. Valente, M. E. Belowich, M. G. Organ, et al. Pd-PEPPSI Complexes and the Negishi Reaction. [J] Eur. J. Org. Chem,2010,23,4343-4354.
[53]George T. Achonduh, Niloufar Hadei, Michael G. Organ, et al. On the role of additives in alkyl-alkyl Negishi cross-couplings. [J] Chem. Commun,2010,46,4109—4111
[54]Wolfgang A. Herrmann, Martina Elison, Georg R. J. Artus. et al. Metal Complexes of N-Heterocyclic Carbenes—A New Structural Principle for Catalysts in Homogeneous Catalysis.[J] Angewandte Chemie International Edition in English.1995,34(21),2371-22374
[55]Guang-Rong Peh, Eric Assen B. Kantchev, Jackie Y. Ying. et al. N-heterocycle carbene (NHC)-ligated cyclopalladated N,N-dimethylbenzylamine:a highly active, practical and versatile catalyst for the Heck-Mizoroki reaction. [J] Org. Biomol. Chem,2009,7,2110-2119
[56]Ming-Tao Ma, Jian-Mei Lu. Dinuclear Pd(II)-NHC complex derived from proline and its application toward Mizoroki-Heck reaction performed in water. [J] Appl. Organometal. Chem. 2012,26,175-179
[57]Ting-Ting Gao, Ai-Ping Jin and Li-Xiong Shao. N-Heterocyclic carbene-palladium(Ⅱ)-1-methyl-imidazole complex catalyzed Mizoroki-Heck reaction of aryl chlorides with styrenes. [J] Beilstein J. Org. Chem.2012,8,1916-1919.
[58]S. Caddick, F. G. N. Cloke, M. R. V. Williams, et al. An improved synthesis of bis(1,3-di-N-tert-butylimidazol-2-ylidene)palladium(0) and its use in C-C and C-N coupling reactions [J]J. Organomet. Chem.,2001,617-618,635-639.
[59]Manoja K. Samantaray, Mobin M. Shaikh, Prasenjit Ghosh. Copper-free and amine-free Sonogashira coupling in air in a mixed aqueous medium by palladium complexes of N/O-functionalized N-heterocyclic carbenes. [J] J. Organomet. Chem.,2001,617-618,635-639.
[60]Fen-Tair Luo, Hung-Kun Lo. Short synthesis of bis-NHC-Pd catalyst derived from caffeine and its applicationsto Suzuki, Heck, and Sonogashira reactions in aqueous solution. [J] J. Organomet. Chem.,2011,696,1262-1265.
[61]Anthony Chartoire, Xavier Frogneux, Steven P. Nolan, et al. [Pd(IPr*)(3-Cl-pyridinyl)Cl2]: A Novel and Efficient PEPPSI Precatalyst. [J] Organometallics.2012,31,6947-6951
[62]Anthony Chartoire, Xavier Frogneux, Steven P. Nolan. An Efficient Palladium-NHC (NHC = N-Heterocyclic Carbene) and Aryl Amination Pre-Catalyst:[Pd (IPr*) (cinnamyl)Cl]. [J] Adv. Synth. Catal.2012,354,1897-1901
[63]Anthony Chartoire, Arnaud Boreux, Steven P. Nolan, et al. Solvent-free aryl amination catalysed by [Pd(NHC)]complexes. [J] RSC Adv.,2013,3,3840-3843
[64]Michael G. Organ, Mirvat Abdel-Hadi, Stephanie Avola. et al. Pd-Catalyzed Aryl AminationMediated by Well Defined, N-HeterocyclicCarbene (NHC)-PdPrecatalysts, PEPPSI. [J] Chem. Eur. J.2008,14,2443-2452
[65]Ka Hou Hoi, Jennifer A. Coggan, Michael G. Organ. Pd-PEPPSI-IPentcl:An Effective Catalyst for the Preparation of Triarylamines. [J] Chem. Eur. J.2013,19,843-845
[66]Tao Tu, Weiwei Fang, Jian Jiang. A highly efficient precatalyst for amination of aryl chlorides:synthesis,structure and application of a robust a cenaphthoimidazolyli-dene palladium complex. [J] Chem. Commun.,2011,47, 12358-12360
[67]Lei Zhu, Ting-Ting Gao, Li-Xiong Shao. Well-defined NHCePd(Ⅱ)eIm (NHC= N-heterocyclic carbene; Im= 1-methylimidazole) complexes catalyzed amination of aryl chlorides. [J] Tetrahedron,2011,67,5150-5155.
[68]Wen-Xin Chen, Li-Xiong Shao. N-Heterocyclic Carbene-Palladium(Ⅱ)-1-Methyl-imidazole Complex Catalyzed Amination between Aryl Chlorides and Amides. [J] J. Org. Chem. 2012,77,9236-9239
[69]S. Suwanprasop, T. Nhujak, S. Roengsumran, A. Petsom, Petroleum Marker Dyes Synthesized from Cardanol and Aniline Derivatives. [J] Ind. Eng. Chem. Res.,2004,43, 4973-4978
[70]Xiaowei Hao, Jia Yuan, Sheng-Hua Liu. et al. Air-stable and highly efficient indenyl-derived phosphine ligand:Application to Buchwald eHartwig amination reactions. [J] Journal of Organo metallic Chemistry.2012,706-707,99-105.
[71]Xusheng Shao, Philip W. Lee, Xuhong Qian. et al. cis-Configuration:A New Tactic/Rationale for Neonicotinoid Molecular Design. [J] J. Agric. Food Chem.,2011,59 (7), 2943-2949
[72]Wenmu Li, Shenghai Li, Suobo Zhang, et al. Synthesis of Bis(amine anhydride)s for Novel High Tgs and Organosoluble Poly(amine imide)s by Palladium-Catalyzed Amination of 4-Chlorophthalide Anhydride. [J] Macromolecules,2007,40 (23),8205-8211
[73]S. A. Lawrence, Amines:Synthesis,Properties and Application. [M] CambridgeUniversity Press, Cambridge,2004;
[74]M. B. Smith, J. March. March's Advanced Organic Chemistry:Reactions, Mechanisms and Structure. [M] John Wiley & Sons Inc.,New Y ork,5th e dn,2001;
[75]H.Heaney. The Benzyne and Related Intermediates. [J] Chem. Rev.,1962,62,81.
[76]J. F. Hartwig, E. I. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis. [M] Wiley-Interscience, New York,2002;
[77]J. F. Hartwig, A. Ricci, Modern Amination Methods. [M] Wiley-VCH, Weinheim,2000.
[78]Masanori Kosugil, Masayuki Kameyama, Toshihiko Migita. Palladium-catalyzed aromatic amination of aryl bromides with N,N-di-ethylamino-tributylin. [J] T. Chem. Lett.1983,927
[79]Anil S. Guram, Roger A. Rennels, Stephen L. Buchwald. A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines. [J] An gew. Chem. Int. Ed.1995,34(12). 1348-1350.
[80]Janis Louie, John F. Hartwig. Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents. [J] Tetrahedron. Lett.1995, 36(21),3609-3612
[81]John F. Hartwig. Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates:Scope and Mechanism. [J] Angew. Chem. Int. Ed.1998, 37(15).2046-2067.
[82]David S. Surry, Stephen L. Buchwald. Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide. [J] Chem. Sci.,2011,2,27-50.
[83]Sebastien Meiries, Klaus Speck, Steven P. Nolan, et al. [Pd(IPr*OMe)(acac)Cl]:Tuning the N-Heterocyclic Carbene in Catalytic C-N Bond Formation. [J] Organometallics.2013,32,330-339
[84]Sebastien Meiries, Anthony Chartoire, Steven P. Nolan, et al. [Pd(IPr*)(acac)Cl]:An Easily Synthesized, Bulky Precatalyst for C-NBond Formation. [J] Organometallics.2012,31,3402-3409
[85]Weiwei Fang, Jian Jiang, Tao Tu. et al. Novel robust benzimidaz olylidene palladium complexes:synthesis structure, and catalytic applications in aminati on of chloroarenes. [J] Tetrahedron.2013,69,673-679.
[86]Stephanie Ho, Ganna Bondarenko, Arturo Orellana. et al. Synthesis of Acyl Pyrroles via Palladium-Catalyzed Carbonylative Amination of Aryl and Alkenyl Iodides. [J] J. Org. Chem. 2012,77,2008-2012
[87]Sarim Dastgir,*Karl S. Coleman, Malcolm L. H. Green*, et al. Synthesis, Structure, and Temperature-Dependent Dynamics of Neutral Palladium Allyl Complexes of Annulated Diaminocarbenes and Their Catalytic Application for C-C and C-N Bond Formation Reactions. [J] Organometallics.2010,29,4858-4870.
[88]Kalyan V. Vasudevan, Rachel R. Butorac, Alan H. Cowley*. et al. Synthesis and coordination compounds of a bis(imino)acenaphthene (BI AN)-supported N-heterocyclic carbene. [J] Dalton Trans.,2010,39,7401-7408.
[89]Christopher J. O4Brien, Eric Assen B. Kantchev, Michael G. Organ*, et al. Easily Prepared Air-and Moisture-Stable Pd-NHC (NHC= N-Heterocyclic Carbene) Complexes:A Reliable, User-Friendly, Highly Active PalladiumPrecatalyst for the Suzuki-Miyaura Reaction. [J] Chem. Eur. J.2006,12,4743-4748
[90]Cecilia A. Citadelle, Erwan Le Nouy, Catherine S. J. Cazin. et al. Simple and versatile synthesis of copper and silver N-heterocyclic carbene complexes in water or organic solvents. [J] Dalton Trans.,2010,39,4489-4491
[91]Marc R. L. Furst and Catherine S. J. Cazin. Copper N-heterocyclic carbene (NHC) complexes as carbene transfer reagents. [J] Chem. Commun.,2010,46,6924-6925
[92]Ming-Tsz Chen, David A. Vicic, Oscar Navarro*. et al. (N-Heterocyclic Carbene) PdCl2(TEA) Complexes:Studies on the Effect of the "Throw-Away" Ligand in Catalytic Activity. [J] Organometallics,2011,30 (18),5052-5056