报道了一种甲苯中醋酸钯催化无配体的Suzuki反应体系.以K3PO4·7H2O为碱,住该体系中可高效进行芳基溴代物和芳基硼酸的Suzuki反应,且具有反应条什温和、无需惰性气体保护等特点.在n(ArBr)=0.5 mmol,n(ArB(OH)2)=0.75 mmol,x(Pd(Oac)2)=1mol%,n(K3PO4·7H2O)=1.0mmol,v(甲苯)=2ml的优化条件下,4.溴硝基苯和苯硼酸住75℃反应5min,分离收率即达99%,TOF高达1 188hM-1.
参考文献
[1] | Miyaura N;Yamada K;Suzuki A .[J].Tetrahedron Letters,1979,36:3437. |
[2] | Miyaura N;Suzuki A .[J].Chemical Reviews,1995,95:2457. |
[3] | Suzuki A. .Cross-coupling reactions via organoboranes[J].Journal of Organometallic Chemistry,2002(1/2):83-90. |
[4] | Kotha S;Lahiri K;Kashinath D .[J].Tetrahedron,2002,58:9633. |
[5] | Li C J .[J].Angewandte Chemie International Edition,2003,42:4856. |
[6] | 黄钟斌,严新焕,江玲超,蒋虹.高效组合型Pd/C催化剂用于Suzuki偶联反应[J].催化学报,2010(01):90-94. |
[7] | 刘春,倪祁健,胡萍萍,袁浩,金子林.水溶性亚胺配体/钯催化的室温Suzuki反应[J].催化学报,2010(10):1277-1280. |
[8] | Hassan J;Sevignon M;Gozzi C;Schulz E Lemaire M .[J].Chemical Reviews,2002,102:1359. |
[9] | Nakamura I;Yamamoto Y .[J].Chemical Reviews,2004,104:2t27. |
[10] | van der Boom M E;Milstein D .[J].Chemical Reviews,2003,103:1759. |
[11] | Barder T E;Walker S D;Martinelli J R;Buchwald S L .[J].Journal of the American Chemical Society,2005,127:4685. |
[12] | Christmann U;Vilar R;Angew Chem .[J].Int Ed,2005,44:366. |
[13] | 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(04):335-338. |
[14] | Zhou, W.-J.;Wang, K.-H.;Wang, J.-X.;Gao, Z.-R. .Ligand-free, atom-efficient Suzuki-Miyaura type cross-coupling reactions at room temperature[J].Tetrahedron,2010(38):7633-7641. |
[15] | Kitamura Y;Sako S;Tsutsui A;Monguehi Y Maegawa T Kitade Y Sajiki H .[J].Advanced Synthesis and Catalysis,2010,352:718. |
[16] | Han W;Liu C;Jin ZL .In situ generation of palladium nanoparticles: A simple and highly active protocol for oxygen-promoted ligand-free suzuki coupling reaction of aryl chlorides[J].Organic letters,2007(20):4005-4007. |
[17] | Han W;Liu C;Jin ZL .Aerobic ligand-free Suzuki coupling reaction of aryl chlorides catalyzed by in situ generated palladium nanoparticles at room temperature[J].Advanced synthesis & catalysis,2008(3):501-508. |
[18] | Alimardanov A;de Vondervoort L S V;de Vries A H M;de Vries J G .[J].Advanced Synthesis and Catalysis,2004,346:1812. |
[19] | Liu C;Yang W B.[J].Chemical Communications,2009:6267. |
[20] | Del Zotto A;Amoroso F;Baratta W;Rigo P .Very Fast Suzuki-Miyaura Reaction Catalyzed by Pd(OAc)(2) under Aerobic Conditions at Room Temperature in EGME/H2O[J].European journal of organic chemistry,2009(1):110-116. |
[21] | Chiang W Y;Hong F E .[J].Journal of Organometallic Chemistry,2009,694:1473. |
[22] | Ullah E;McNulty J;Robertson A .[J].Tetrahedron Letters,2009,50:5599. |
[23] | Chandrasekhar, V;Narayanan, RS;Thilagar, P .Organostannoxane-Supported Palladium Nanoparticles. Highly Efficient Catalysts for Suzuki-Coupling Reactions[J].Organometallics,2009(20):5883-5888. |
[24] | Pan C D;Liu M C;Zhang L;Wu H Y Ding J C Cheng J .[J].Catalysis Communications,2008,9:508. |
[25] | Leadbeater N E;Marco M .[J].Organic Letters,2002,4:2973. |
[26] | Venkatraman S;Li C J .[J].Organic Letters,1999,1:1133. |
[27] | Kapoor S.;Joshi R.;Mukherjee T. .Influence of I- anions on the formation and stabilization of copper nanoparticles[J].Chemical Physics Letters,2002(5-6):443-448. |
[28] | Saha D;Chattopadhyay K;Ranu B C .[J].Tetrahedron Letters,2009,50:1003. |
[29] | Zhang HC.;Tian Y.;Chan KS.;Kwong FY. .Base and cation effects on the Suzuki cross-coupling of bulky arylboronic acid with halopyridines: Synthesis of pyridylphenols[J].The Journal of Organic Chemistry,1998(20):6886-6890. |
[30] | Kitamura Y;Sako S;Udzu T;Tsutsui A;Maegawa T;Monguchi Y;Sajiki H .Ligand-free Pd/C-catalyzed Suzuki-Miyaura coupling reaction for the synthesis of heterobiaryl derivatives[J].Chemical communications,2007(47):5069-5071. |
[31] | Klingensmith L M;Leadbeater N E .[J].Tetrahedron Letters,2003,44:765. |
[32] | Zhang HC.;Costanzo MJ.;Lawson EC.;Maryanoff CA.;Maryanoff BE.;Harris BD. .Stereocontrol between remote atom centers in acyclic substrates. Anti addition of hydride to 1,5-, 1,6-, and 1,7-hydroxy ketones[J].The Journal of Organic Chemistry,1998(22):7964-7981. |
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