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水溶性亚胺配体/钯催化的室温Suzuki反应 被引量:2

Water-Soluble Imine Ligand/Palladium-Catalyzed Suzuki Reaction at Room Temperature
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摘要 设计并合成了一种新型水溶性亚胺双齿配体I,并得到其单晶结构.该配体具有半配位效应和绿色化学特征,与氯化钯组成的催化体系在空气和室温条件下,可有效催化乙醇水溶液中的溴代芳烃与芳基硼酸的Suzuki交叉偶联反应.在n(ArBr)=0.5mmol,n(ArB(OH)2)=0.75mmol,x(PdCl2)=1%,x(I)=2%,n(K2CO3)=1.0mmol,c(EtOH)=50%水溶液的优化条件下,经20min反应,分离收率即可达到99%. A new air-stable and water-soluble imine ligand (I) has been synthesized and its single crystal structure has been characterized. This N,O-bidentate ligand, with the possible hemilability and the property of green chemistry, is efficient in the palladium-catalyzed Suzuki cross-coupling of aryl bromide and aryl-boronic acid at room temperature in aqueous ethanol. Under the optimized reaction conditions (i.e., n(ArBr) = 0.5 mmol, n(ArB(OH)2) = 0.75 mmol, x(PdCl2) = 1%, x(I) = 2 mol%, n(K2CO3) = 1.0 mmol, and c(EtOH) = 50% aqueous solu-tion), a 99% isolated yield of the product was obtained in 20 min.
出处 《催化学报》 SCIE CAS CSCD 北大核心 2010年第10期1277-1280,共4页
基金 国家自然科学基金(20976024 20923006) 教育部长江学者和创新团队发展计划(IRT0711) 精细化工国家重点实验室开放课题(KF0801) 大连理工大学理学研究基金及研究生教育改革基金
关键词 SUZUKI反应 交叉偶联 亚胺配体 水相 Suzuki reaction cross-coupling imine ligand palladium aqueous media
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参考文献24

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同被引文献14

  • 1周浩,卓广澜,姜玄珍,张波,葛忠华.无配体Pd/LDH-F催化剂在Heck和Suzuki反应中的应用[J].催化学报,2006,27(4):335-338. 被引量:6
  • 2Sawant A D,Dilip G R,Nitin B D. An Ester Appending Multifunctional Ionic Liquid for Pd(Ⅱ)Catalyzed Heck Reaction[J].Cat Commu,2010,(04):273-276.
  • 3Abdol R H,Fatemeh R. Accelerated Heck Reaction Using Ortho-Palladated Complex in a Non-Aqueous Ionic Liquid with Controlled Microwave Heating[J].Applied Organometallic Chemistry,2011,(07):542-551.
  • 4Billingsley K,Buchwald S L. Highly Efficient Monophosphine-Based Catalyst for the Palladium-Catalyzed Suzuki-Miyaura Reaction of Heteroaryl Halides and Heteroaryl Boronic Acids and Esters[J].Journal of the American Chemical Society,2007,(11):3358-3366.
  • 5Martin R,Buchwald S L. Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands[J].Accounts of Chemical Research,2008,(11):1461-1473.
  • 6Sawai K,Tatumi R,Nakahodo T. Asymmetric Suzuki-Miyaura Coupling Reactions Catalyzed by Chiral Palladium Nanoparticles at Room Temperature[J].Angewandte Chemie International Edition,2008,(36):6917-6919.
  • 7Desimone J M. Practical Approaches to Green Solvents[J].Science,2002,(5582):799-803.doi:10.1126/science.1069622.
  • 8Yang H Q,Han X J,Ma Z C. Palladium-Guanidine Complex Immobilized on SBA-16:a Highly Active and Recyclable Catalyst for Suzuki Coupling and Alcohol Oxidation[J].Green Chemistry,2010,(03):441-451.
  • 9Liu L F,Zhang Y H,Xin B W. Synthesis of Biaryls and Polyaryls by Ligand-Free Suzuki Reaction in Aqueous Phase[J].Journal of Organic Chemistry,2006.3994-3398.
  • 10Liu L,Zhang Y,Wang Y. Phosphine-Free Palladium Acetate Catalyzed Suzuki Reaction in Water[J].Journal of Organic Chemistry,2005,(15):6122-6125.

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