Palladium-catalyzed cross-coupling reaction of potassium diaryldifluoroborates with aryl halides

被引:19
作者
Ito, T [1 ]
Iwai, T [1 ]
Mizuno, T [1 ]
Ishino, Y [1 ]
机构
[1] Osaka Municipal Tech Res Inst, Joto Ku, Osaka 5368553, Japan
关键词
Grignard reactions; cross-coupling; organoborate; biaryls; arylations;
D O I
10.1055/s-2003-40851
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic cross-coupling reaction of potassium diaryldiluoroborates with aryl halides proceeds to afford the, biphenyls in good yields. These salts on an arylation reagent were readily prepared via a protocol of the Grignard method and transformation to potassium salts. Two aryl groups of these salts were efficiently transferred in the Suzuki-Miyaura reaction.
引用
收藏
页码:1435 / 1438
页数:4
相关论文
共 21 条
[1]   DEPHENYLATION REACTIONS OF PHENYLBORON ACIDS AND ESTERS [J].
ABEL, EW ;
GERRARD, W ;
LAPPERT, MF .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (APR) :1451-1453
[2]   Synthesis and cross-coupling reactions of tetra alkylammonium organotrifluoroborate salts [J].
Batey, RA ;
Quach, TD .
TETRAHEDRON LETTERS, 2001, 42 (52) :9099-9103
[3]   Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls [J].
Baudoin, O ;
Guénard, D ;
Guéritte, F .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9268-9271
[4]   Phosphine-free palladium-catalyzed cross-coupling of tris(1-naphthyl)borane with aryl halides and iodonium salts [J].
Bumagin, NA ;
Tsarev, DA .
TETRAHEDRON LETTERS, 1998, 39 (44) :8155-8158
[5]   Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes [J].
Bumagin, NA ;
Korolev, DN .
TETRAHEDRON LETTERS, 1999, 40 (15) :3057-3060
[6]   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
[7]  
Bumagin NA, 1996, ZH OBSHCH KHIM+, V66, P1981
[8]  
BUMAGIN NA, 1995, IAN SSSR KH, P394
[9]   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
[10]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469