Palladium-Catalyzed Suzuki-Miyaura Type Coupling Reaction of Aryl Halides with Triphenylborane-Pyridine

被引:1
作者
Yang Minghua [1 ]
Gu Yongbing [1 ]
Wang Yan [1 ]
Zhao Xiyu [1 ]
Yan Guobing [1 ]
机构
[1] Lishui Univ, Dept Chem, Lishui 323000, Zhejiang, Peoples R China
关键词
triphenylbroane-pyridine; Suzuki-Miyaura coupling; aryl halides; palladium catalysts; BORONIC ACIDS; CONVENIENT; COMPLEXES; COMBINATION; ARENES;
D O I
10.1002/cjoc.201200775
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Suzuki-Miyaura type coupling reaction of aryl halides with triphenylborane-pyridine was described. The reaction can be catalyzed by Pd(OAc)2 (5 mol%) in presence of Cs2CO3 at 50 degrees C or 80 degrees C, and functionalized biaryls were obtained in good to excellent yields. This protocol is general and can tolerate a wide range of functional groups.
引用
收藏
页码:2581 / 2586
页数:6
相关论文
共 27 条
[1]   Dichloro-Bis(aminophosphine) Complexes of Palladium: Highly Convenient, Reliable and Extremely Active Suzuki-Miyaura Catalysts with Excellent Functional Group Tolerance [J].
Bolliger, Jeanne L. ;
Frech, Christian M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (13) :4075-4081
[2]   Highly practical boronic acid surrogates for the Suzuki-Miyaura cross-coupling [J].
Bonin, Helene ;
Leuma-Yona, Rodrigue ;
Marchiori, Bruno ;
Demonchaux, Patrice ;
Gras, Emmanuel .
TETRAHEDRON LETTERS, 2011, 52 (10) :1132-1135
[3]   Base free aryl coupling of diazonium compounds and boronic esters: self-activation allowing an overall highly practical process [J].
Bonin, Helene ;
Delbrayelle, Dominique ;
Demonchaux, Patrice ;
Gras, Emmanuel .
CHEMICAL COMMUNICATIONS, 2010, 46 (15) :2677-2679
[4]   ORGANOBORANES .43. A CONVENIENT, HIGHLY EFFICIENT SYNTHESIS OF TRIORGANYLBORANES VIA A MODIFIED ORGANOMETALLIC ROUTE [J].
BROWN, HC ;
RACHERLA, US .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :427-432
[5]   Ligandless palladium catalyzed reactions of arylboronic acids and sodium tetraphenylborate with aryl halides in aqueous media [J].
Bumagin, NA ;
Bykov, VV .
TETRAHEDRON, 1997, 53 (42) :14437-14450
[6]   Aryl trihydroxyborates: Easily isolated discrete species convenient for direct application in coupling reactions [J].
Cammidge, Andrew N. ;
Goddard, Victoria H. M. ;
Gopee, Hemant ;
Harrison, Nicola L. ;
Hughes, David L. ;
Schubert, Christopher J. ;
Sutton, Benjamin M. ;
Watts, Gary L. ;
Whitehead, Andrew J. .
ORGANIC LETTERS, 2006, 8 (18) :4071-4074
[7]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF VINYL AND ARYL TRIFLATES WITH TETRAARYLBORATES [J].
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1992, 33 (33) :4815-4818
[8]   Potassium organotrifluoroborates: New perspectives in organic synthesis [J].
Darses, Sylvain ;
Genet, Jean-Pierre .
CHEMICAL REVIEWS, 2008, 108 (01) :288-325
[9]  
Doe I. S., 1968, J AM CHEM SOC, V90, P8234
[10]   Regioselective Synthesis and Slow-Release Suzuki-Miyaura Cross-Coupling of MIDA Boronate-Functionalized Isoxazoles and Triazoles [J].
Grob, Jonathan E. ;
Nunez, Jill ;
Dechantsreiter, Michael A. ;
Hamann, Lawrence G. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (24) :10241-10248