Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis

被引：109

作者：

Broutin, PE ^{[1
]}

Cerna, I ^{[1
]}

Campaniello, M ^{[1
]}

Leroux, F ^{[1
]}

Colobert, F ^{[1
]}

机构：

[1] Univ Strasbourg 1, ECPM, CNRS, UMR 7008,Lab Stereochim, F-67087 Strasbourg 2, France

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 24期

关键词：

D O I：

10.1021/ol048303b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The coupling reaction of pinacolborane with various aryl bromides in the presence of a catalytic amount of Pd(OAc)(2) together with DPEphos as ligand and Et3N as base provided arylboronates. High yields were obtained in the case of electron-donor substituted aryl bromides. The direct preparation of arylboronates allowed the one-pot, two-step synthesis of unsymmetrical biaryls in high yields.

引用

页码：4419 / 4422

页数：4

共 23 条

[1] Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls
Baudoin, O
Guénard, D
Guéritte, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) : 9268 - 9271
[2] Novel concepts in directed biaryl synthesis, part 78. The lactone concept: An efficient pathway to axially chiral natural products and useful reagents
Bringmann, G
Breuning, M
Tasler, S
[J]. SYNTHESIS-STUTTGART, 1999, (04): : 525 - 558
[3] Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[4] PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES
ECHAVARREN, AM
STILLE, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) : 1557 - 1565
[5] Farina V., 1995, COMPREHENSIVE ORGANO, V12, P161
[6] Synthesis of arylboronates via the palladium(O)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflates
Ishiyama, T
Itoh, Y
Kitano, T
Miyaura, N
[J]. TETRAHEDRON LETTERS, 1997, 38 (19) : 3447 - 3450
[7] PALLADIUM(O)-CATALYZED CROSS-COUPLING REACTION OF ALKOXYDIBORON WITH HALOARENES - A DIRECT PROCEDURE FOR ARYLBORONIC ESTERS
ISHIYAMA, T
MURATA, M
MIYAURA, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) : 7508 - 7510
[8] NEW DIPHOSPHINE LIGANDS BASED ON HETEROCYCLIC AROMATICS INDUCING VERY HIGH REGIOSELECTIVITY IN RHODIUM-CATALYZED HYDROFORMYLATION - EFFECT OF THE BITE ANGLE
KRANENBURG, M
VANDERBURGT, YEM
KAMER, PCJ
VANLEEUWEN, PWNM
GOUBITZ, K
FRAANJE, J
[J]. ORGANOMETALLICS, 1995, 14 (06) : 3081 - 3089
[9] MATTESON DS, 1987, CHEM METAL CARBON BO, V4, P307
[10] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS
MIYAURA, N
SUZUKI, A
[J]. CHEMICAL REVIEWS, 1995, 95 (07) : 2457 - 2483

← 1 2 3 →