Palladium-catalyzed silylation of aryl chlorides with hexamethyldisilane

被引：77

作者：

McNeill, Eric ^{[1
]}

Barder, Timothy E. ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 19期

关键词：

D O I：

10.1021/ol701518f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the palladium-catalyzed silylation of aryl chlorides has been developed. The method affords desired product in good yield, is tolerant of a variety of functional groups, and provides access to a wide variety of aryltrimethylsilanes from commercially available aryl chlorides. Additionally, a one-pot procedure that converts aryl chlorides into aryl iodides has been developed.

引用

页码：3785 / 3788

页数：4

共 24 条

[1] Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles
Anderson, Kevin W.
Tundel, Rachel E.
Ikawa, Takashi
Altman, Ryan A.
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) : 6523 - 6527
[2] REACTIONS OF ORGANIC HALIDES WITH R3MMR3 COMPOUNDS (M=SI,GE,SN) IN PRESENCE OF TETRAKIS(TRIARYLPHOSPHINE) PALLADIUM
AZARIAN, D
DUA, SS
EABORN, C
WALTON, DRM
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 117 (03) : C55 - C57
[3] SYNTHESIS OF ARYLSILANE AND HETEROARYLSILANE BY CLEAVAGE OF HEXAMETHYLDILANE
BABIN, P
BENNETAU, B
THEURIG, M
DUNOGUES, J
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 446 (1-2) : 135 - 138
[4] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters
Billingsley, Kelvin
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) : 3358 - 3366
[5] Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects
Burgos, Carlos H.
Barder, Timothy E.
Huang, Xiaohua
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4321 - 4326
[6] REVERSE HALOGENATION USING SUPPORTED COPPER(I) IODIDE
CLARK, JH
JONES, CW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (18) : 1409 - 1410
[7] ELECTROCHEMICAL TRIMETHYLSILYLATION OF O-DICHLOROBENZENE - A SELECTIVE ROUTE TO SILYLATED CYCLO-C6 SYNTHONS
DEFFIEUX, D
BORDEAU, M
BIRAN, CL
DUNOGUES, J
[J]. ORGANOMETALLICS, 1994, 13 (06) : 2415 - 2422
[8] Palladium-catalyzed silylation of aryl bromides leading to functionalized aryldimethylsilanols
Denmark, SE
Kallemeyn, JM
[J]. ORGANIC LETTERS, 2003, 5 (19) : 3483 - 3486
[9] FURTHER-STUDIES ON REACTIONS OF ORGANIC HALIDES WITH DISILANES CATALYZED BY TRANSITION-METAL COMPLEXES
EABORN, C
GRIFFITHS, RW
PIDCOCK, A
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 225 (01) : 331 - 341
[10] Goossen LJ, 2000, SYNLETT, P1801

← 1 2 3 →