葡萄糖修饰的Salen在微波加热Pd-催化水中的Suzuki反应中的应用
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摘要
本文通过改进文献方法合成了葡萄糖修饰的Salen类似物,并将其应用于微波加热Pd-催化的水中Suzuki反应。通过对不同温度、辅助碱以及相转移催化剂等条件的考察,发现在150oC、K2CO3为辅助碱,TBAB为相转移催化剂条件下,反应3 min即可获得理想的收率。这一反应条件也同样适合于取代溴苯与取代苯硼酸的偶联反应。产物与水相分离后,水相继续重复使用,在前2次的循环使用中,催化体系保持了很好的催化活性。
A glucose modified Salen analogue was synthesized by improved literature protocol.This compound coordinated with palladium as catalyst for the Suzuki reaction which was heated by microwave. The influences of reaction temperature,base and phase transfer catalyst on the Suzuki reaction of bromobenzene and phenylboronic acid were investigated.Based on the experimental results and considering of the cost of started materials,the optimal reaction condition was that the base was K2 CO3,the phase transfer catalyst was tetra-butyl ammonium bromide( TBAB) and the reaction time was 3 minutes.Under the optimal condition,the Suzuki reactions of aryl bromide and aryl boronic acid were fulfilled with good to excellent yield. At the same reaction condition,the catalytic system was cyclic used 3 times,the catalytic activities of aqueous phase in the first two cyclic use were still good.
A glucose modified Salen analogue was synthesized by improved literature protocol.This compound coordinated with palladium as catalyst for the Suzuki reaction which was heated by microwave. The influences of reaction temperature,base and phase transfer catalyst on the Suzuki reaction of bromobenzene and phenylboronic acid were investigated.Based on the experimental results and considering of the cost of started materials,the optimal reaction condition was that the base was K2 CO3,the phase transfer catalyst was tetra-butyl ammonium bromide( TBAB) and the reaction time was 3 minutes.Under the optimal condition,the Suzuki reactions of aryl bromide and aryl boronic acid were fulfilled with good to excellent yield. At the same reaction condition,the catalytic system was cyclic used 3 times,the catalytic activities of aqueous phase in the first two cyclic use were still good.
引文
[1]Miyaura N,Yamada K,Suzuki A. A new stereospecific cross-coupling by palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides[J]. Tetrahedron Lett,1979,26:3 437-3 440.
[2]Miyaura N,Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds[J].Chem Rev,1995,95:2 457-2 483.
[3]Suzuki A.Cross-coupling reactions via organoboranes[J].J Organomet Chem,2002,653:83-90.
[4]Li C-J.Suzuki reaction takes a“Naked Hot Bath”:coupling in high-temperature water without transition metals[J].Angew Chem Int Ed,2003,42:4 856-4 858.
[5]Lundin PM,Fu GC.Asymmetric Suzuki cross-coupling of activated seconedary alkyl electrophiles:arylation of racemicα-chloroamides[J]. J Am Chem Soc,2010,132:11027-11 029.
[6]Shen X,Jones GO,Watson DA,et al.Enantioselective synthesis of axially chiral biaryls by the Pd-catalyzed SuzukiMiyaura reaction:Substrate scope and quantum mechanicl investigation[J]. J Am Chem Soc,2010,132:11 278-11287.
[7]刘宁,刘春,金子林,水相钯催化Suzuki反应[J].有机化学,2012,32:860-876.
[8]Bellina F,Carpita A,Rossi R.Palladium catalysts for Suzuki cross-coupling reaction:an overview of recent advances[J].Synthesis,2004,(15):2 419-2 440.
[9]Dupontn J,de Souza RF,Suarez PAZ.Ionic liquid(molten salt)phase organometallic catalysis[J]. Chem Rev,2002,102:3 667-3 692.
[10]Leeke G A,Al-Duri B,Seville JPK,et al.Continuous-flow Suzuki-Miyaura reaction in supercritical carbon dioxide[J].Org Process Res Dev,2007,11:144-148.
[11]Watanabe M,Sato T,Inomata H,et al.Chemical reactions of C1 compounds in near-critical and supercritical water[J].Chem Rev,2004,104:5 803-5 822.
[12]Curran DP.Fluorous chemistry in Pittsburgh:1996-2008[J].J Fluorine Chem,2008,129:898-902.
[13]赵晓伟,崔元成,微波技术在Suzuki反应中的应用[J].化学进展,2006,18:1 652-1 658.
[14]Kappe CO. Controlled microwave heating in modern organic synthesis[J].Angew Chem Int Ed,2004,43:6 250-6 284.
[15]Leadbeater NE,Marco M. Transition-metal-free Suzukitype reactions[J].Angew Chem Int Ed,2003,42:1 407-1409.
[16]孙斌.PdCl2催化微波促进的水中的Heck反应研究[J].化学研究与应用,2017,29:968-973。
[17]孙斌,向鹏,水-有机两项体系中Pd(OAc)2催化的Suzuki反应与2-(4-氯苯基)苯胺的合成[J].化学研究与应用,2014,26:1 318-1 323.
[18]孙斌,郭秦.一种啶酰菌胺的制备方法[P]. CN:201410298571.8,2016-03-20.
[19]Storr T,Merkel M,Song-Zhao GX,et al.Synthesis,characterization,and metal coordinating ability of multifunctional carbohydrate-containing compounds for Alzheimer’s therapy[J].J Am Chem Soc,2007,129:7 453-7 463.
[20]Sedighipoor M,Kianfar AH,Mohammadnezhad G,et al.Unsymmetrical palladium(II)N,N,O,O-Schiff base complexes:efficient catalysts for Suzuki coupling reaction[J].Inorg Chim Acta,2018,476:20-26.
[21]Leadbeater NE.Fast,easy,chean chemistry by using water as a solvent and microwave heating:the Suzuki coupling as an illustration[J]. Chem Commun,2005,41:2881-2 902.
[22]Martínez-Klimov ME,Hernández-Hipólito PH,MariínezGarcía M,et al.Pd catalysts supported on hydrogen titanate nanotubes for Suzuki-Miyaura cross-coupling reactions[J].Catal Today,2018,305:58-64.
[23]More than just a support:Graphene as a solid-state ligand for palladium-catalyzed cross-coupling reactions[J]. J Catal,2018,360:20-26.
[24]Arvela RK,Leadbeater NE.Suzuki coupling of aryl chloride with phenylboronic acid in water,using microwave heating with simultaneous cooling[J].Org Lett,2005,7:2101-2 104.
[25]刘宁,刘春,金子林.醋酸钯催化甲苯中无配体的Suzuki反应[J].催化学报,2010,31:1 316-1 320.
[2]Miyaura N,Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds[J].Chem Rev,1995,95:2 457-2 483.
[3]Suzuki A.Cross-coupling reactions via organoboranes[J].J Organomet Chem,2002,653:83-90.
[4]Li C-J.Suzuki reaction takes a“Naked Hot Bath”:coupling in high-temperature water without transition metals[J].Angew Chem Int Ed,2003,42:4 856-4 858.
[5]Lundin PM,Fu GC.Asymmetric Suzuki cross-coupling of activated seconedary alkyl electrophiles:arylation of racemicα-chloroamides[J]. J Am Chem Soc,2010,132:11027-11 029.
[6]Shen X,Jones GO,Watson DA,et al.Enantioselective synthesis of axially chiral biaryls by the Pd-catalyzed SuzukiMiyaura reaction:Substrate scope and quantum mechanicl investigation[J]. J Am Chem Soc,2010,132:11 278-11287.
[7]刘宁,刘春,金子林,水相钯催化Suzuki反应[J].有机化学,2012,32:860-876.
[8]Bellina F,Carpita A,Rossi R.Palladium catalysts for Suzuki cross-coupling reaction:an overview of recent advances[J].Synthesis,2004,(15):2 419-2 440.
[9]Dupontn J,de Souza RF,Suarez PAZ.Ionic liquid(molten salt)phase organometallic catalysis[J]. Chem Rev,2002,102:3 667-3 692.
[10]Leeke G A,Al-Duri B,Seville JPK,et al.Continuous-flow Suzuki-Miyaura reaction in supercritical carbon dioxide[J].Org Process Res Dev,2007,11:144-148.
[11]Watanabe M,Sato T,Inomata H,et al.Chemical reactions of C1 compounds in near-critical and supercritical water[J].Chem Rev,2004,104:5 803-5 822.
[12]Curran DP.Fluorous chemistry in Pittsburgh:1996-2008[J].J Fluorine Chem,2008,129:898-902.
[13]赵晓伟,崔元成,微波技术在Suzuki反应中的应用[J].化学进展,2006,18:1 652-1 658.
[14]Kappe CO. Controlled microwave heating in modern organic synthesis[J].Angew Chem Int Ed,2004,43:6 250-6 284.
[15]Leadbeater NE,Marco M. Transition-metal-free Suzukitype reactions[J].Angew Chem Int Ed,2003,42:1 407-1409.
[16]孙斌.PdCl2催化微波促进的水中的Heck反应研究[J].化学研究与应用,2017,29:968-973。
[17]孙斌,向鹏,水-有机两项体系中Pd(OAc)2催化的Suzuki反应与2-(4-氯苯基)苯胺的合成[J].化学研究与应用,2014,26:1 318-1 323.
[18]孙斌,郭秦.一种啶酰菌胺的制备方法[P]. CN:201410298571.8,2016-03-20.
[19]Storr T,Merkel M,Song-Zhao GX,et al.Synthesis,characterization,and metal coordinating ability of multifunctional carbohydrate-containing compounds for Alzheimer’s therapy[J].J Am Chem Soc,2007,129:7 453-7 463.
[20]Sedighipoor M,Kianfar AH,Mohammadnezhad G,et al.Unsymmetrical palladium(II)N,N,O,O-Schiff base complexes:efficient catalysts for Suzuki coupling reaction[J].Inorg Chim Acta,2018,476:20-26.
[21]Leadbeater NE.Fast,easy,chean chemistry by using water as a solvent and microwave heating:the Suzuki coupling as an illustration[J]. Chem Commun,2005,41:2881-2 902.
[22]Martínez-Klimov ME,Hernández-Hipólito PH,MariínezGarcía M,et al.Pd catalysts supported on hydrogen titanate nanotubes for Suzuki-Miyaura cross-coupling reactions[J].Catal Today,2018,305:58-64.
[23]More than just a support:Graphene as a solid-state ligand for palladium-catalyzed cross-coupling reactions[J]. J Catal,2018,360:20-26.
[24]Arvela RK,Leadbeater NE.Suzuki coupling of aryl chloride with phenylboronic acid in water,using microwave heating with simultaneous cooling[J].Org Lett,2005,7:2101-2 104.
[25]刘宁,刘春,金子林.醋酸钯催化甲苯中无配体的Suzuki反应[J].催化学报,2010,31:1 316-1 320.