A synthesis of biaryls via nickel(0)-catalyzed cross-coupling reaction of chloroarenes with phenylboronic acids

被引:156
作者
Saito, S [1 ]
Sakai, M [1 ]
Miyaura, N [1 ]
机构
[1] HOKKAIDO UNIV,FAC ENGN,DIV MOL CHEM,SAPPORO,HOKKAIDO 060,JAPAN
关键词
D O I
10.1016/0040-4039(96)00482-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cross-coupling reaction of phenylboronic acid with chloroarenes to give biaryls was carried out in high yields at 80 degrees C in the presence of the nickel(0) catalyst and K3PO4 (3 equivs) in dioxane. The nickel(0) catalyst prepared in situ from NiCl2(dppf) (10 mol%) and four equivalents of BuLi was recognized to be most effective. The reaction can be applicable for a wide range of chloroarenes having an electron-withdrawing or an electron-donating group such as 4-CN-, 4-CHO, 2- or 4-CO(2)Me, 4-COMe, 4-NHAc, 3- or 4-Me, and 3- or 4-OMe, and 4-NH2. (C) 1996 Elsevier Science Ltd
引用
收藏
页码:2993 / 2996
页数:4
相关论文
共 14 条
[1]   A SHORT ENTRY INTO THE PYRIDO[2,3-B]INDOLE RING-SYSTEM - SYNTHESIS OF THE TETRACYCLIC SEGMENT OF THE MARINE ANTITUMOR AGENTS - GROSSULARINE-1 AND GROSSULARINE-2 [J].
ACHAB, S ;
GUYOT, M ;
POTIER, P .
TETRAHEDRON LETTERS, 1993, 34 (13) :2127-2130
[2]   SYNTHESIS AND RESOLUTION OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE - A P-N CHELATING LIGAND FOR ASYMMETRIC CATALYSIS [J].
ALCOCK, NW ;
BROWN, JM ;
HULMES, DI .
TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :743-756
[3]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ARYLBORONIC ACIDS WITH PI-DEFICIENT HETEROARYL CHLORIDES [J].
ALI, NM ;
MCKILLOP, A ;
MITCHELL, MB ;
REBELO, RA ;
WALLBANK, PJ .
TETRAHEDRON, 1992, 48 (37) :8117-8126
[4]  
[Anonymous], 1991, COMPREHENSIVE ORGANI
[5]  
Farina V., 1995, COMPREHENSIVE ORGANO, V12, P161
[6]   OXIDATIVE ADDITION OF ARYL HALIDES TO TRIS(TRIPHENYLPHOSPHINE)NICKEL(0) [J].
FOA, M ;
CASSAR, L .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1975, (23) :2572-2576
[7]  
JANIETZ D, 1993, SYNTHESIS-STUTTGART, P33
[8]   FACILE ARYL ARYL EXCHANGE BETWEEN THE PALLADIUM CENTER AND PHOSPHINE-LIGANDS IN PALLADIUM(II) COMPLEXES [J].
KONG, KC ;
CHENG, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6313-6315
[9]   COUPLING OF HETEROARYL CHLORIDES WITH ARYLBORONIC ACIDS IN THE PRESENCE OF [1,4-BIS-(DIPHENYLPHOSPHINE)BUTANE]PALLADIUM(II) DICHLORIDE [J].
MITCHELL, MB ;
WALLBANK, PJ .
TETRAHEDRON LETTERS, 1991, 32 (20) :2273-2276
[10]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483