Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)-tricyclohexylphosphine complexes

被引：265

作者：

Ishiyama, T ^{[1
]}

Ishida, K ^{[1
]}

Miyaura, N ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Sapporo, Hokkaido 0608628, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 49期

关键词：

boron and compounds; coupling reactions; aryl halides; palladium and compounds;

D O I：

10.1016/S0040-4020(01)00998-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cross-coupling reaction of bis-(pinacolato)diboron with chloroarenes to yield pinacol arylboronates was carried out in 1,4-dioxane at 80 degreesC in the presence of KOAc (1.5 equiv.) and Pd(dba)(2)/2.4PCy(3) (3-6 mol%). The catalyst was also effective to carry out analogous coupling with aryl bromides or triflates under milder conditions than those of the previous procedures catalyzed by PdCl2(dppf) in DMSO. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：9813 / 9816

页数：4

共 50 条

[41] STERIC EFFECTS OF PHOSPHORUS LIGANDS IN ORGANOMETALLIC CHEMISTRY AND HOMOGENEOUS CATALYSIS
TOLMAN, CA
[J]. CHEMICAL REVIEWS, 1977, 77 (03) : 313 - 348
[42] CHEMISTRY OF DIBENZYLIDENEACETONE-PALLADIUM(0) COMPLEXES .1. NOVEL TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(SOLVENT) COMPLEXES AND THEIR REACTIONS WITH QUINONES
UKAI, T
KAWAZURA, H
ISHII, Y
BONNET, JJ
IBERS, JA
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 65 (02) : 253 - 266
[43] Synthesis, morphology, and optical properties of tetrahedral oligo(phenylenevinylene) materials
Wang, SJ
Oldham, WJ
Hudack, RA
Bazan, GC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (24) : 5695 - 5709
[44] Highly active palladium catalysts for Suzuki coupling reactions
Wolfe, JP
Singer, RA
Yang, BH
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) : 9550 - 9561
[45] Wolfe JP, 1999, ANGEW CHEM INT EDIT, V38, P2413, DOI 10.1002/(SICI)1521-3773(19990816)38:16<2413::AID-ANIE2413>3.0.CO
[46] 2-H
[47] The first optically active BINOL-BINAP copolymer catalyst: Highly stereoselective tandem asymmetric reactions
Yu, HB
Hu, QS
Pu, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) : 6500 - 6501
[48] Total synthesis of robustaflavone, a potential anti-hepatitis B agent
Zembower, DE
Zhang, HP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) : 9300 - 9305
[49] Palladium-bisimidazol-2-ylidene complexes as catalysts for general and efficient Suzuki cross-coupling reactions of aryl chlorides with arylboronic acids
Zhang, CM
Trudell, ML
[J]. TETRAHEDRON LETTERS, 2000, 41 (05) : 595 - 598
[50] Palladium-imidazol-2-ylidene complexes as catalysts for facile and efficient Suzuki cross-coupling reactions of aryl chlorides with arylboronic acids
Zhang, CM
Huang, JK
Trudell, ML
Nolan, SP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) : 3804 - 3805

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