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

被引：155

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

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 17期

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

页码：2993 / 2996

页数：4

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
ACHAB, S
GUYOT, M
POTIER, P
[J]. 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
ALCOCK, NW
BROWN, JM
HULMES, DI
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (04) : 743 - 756
[3] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ARYLBORONIC ACIDS WITH PI-DEFICIENT HETEROARYL CHLORIDES
ALI, NM
MCKILLOP, A
MITCHELL, MB
REBELO, RA
WALLBANK, PJ
[J]. 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)
FOA, M
CASSAR, L
[J]. 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
KONG, KC
CHENG, CH
[J]. 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
MITCHELL, MB
WALLBANK, PJ
[J]. TETRAHEDRON LETTERS, 1991, 32 (20) : 2273 - 2276
[10] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS
MIYAURA, N
SUZUKI, A
[J]. CHEMICAL REVIEWS, 1995, 95 (07) : 2457 - 2483

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