Preparation of Allyl and Vinyl Silanes by the Palladium-Catalyzed Silylation of Terminal Olefins: A Silyl-Heck Reaction

被引：121

作者：

McAtee, Jesse R. ^{[1
]}

Martin, Sara E. S. ^{[1
]}

Ahneman, Derek T. ^{[1
]}

Johnson, Keywan A. ^{[1
]}

Watson, Donald A. ^{[1
]}

机构：

[1] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 15期

基金：

美国国家科学基金会;

关键词：

alkenes; allyl silanes; Heck reaction; palladium; vinyl silanes; CROSS-COUPLING REACTIONS; OXIDATIVE ADDITION; STEREOSELECTIVE-SYNTHESIS; ARYL HALIDES; COMPLEXES; REAGENTS; ALKENES; IODOTRIMETHYLSILANE; ALLYLSILANES; ALDEHYDES;

D O I：

10.1002/anie.201200060

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Installing silicon is easy! A high-yielding protocol for the palladium-catalyzed silylation of terminal alkenes is reported. This method allows facile conversion of styrenes to E-β-silyl styrenes by using iodotrimethylsilane (TMSI) or chlorotrimethylsilane/lithium iodide (see scheme). Terminal allyl silanes with good E/Z ratios are also readily accessed from α-olefins. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3663 / 3667

页数：5

共 56 条

[1]

[Anonymous], 1998, ANGEW CHEM, V110, P2798

[2]

Armitage D.A., 1982, Comprehensive Organometallic Synthesis, V2, P6

[3] Highly β-(E)-selective hydrosilylation of terminal and internal alkynes catalyzed by a (IPr)Pt(diene) complex [J].

Berthon-Gelloz, Guillaume ;

Schumers, Jean-Marc ;

De Bo, Guillaume ;

Marko, Istvan E. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (11) :4190-4197

[4]

Brook M. A., 2000, SILICON ORGANIC ORGA

[5] Allylic C-H Acetoxylation with a 4,5-Diazafluorenone-Ligated Palladium Catalyst: A Ligand-Based Strategy To Achieve Aerobic Catalytic Turnover [J].

Campbell, Alison N. ;

White, Paul B. ;

Guzei, Ilia A. ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) :15116-15119

[6] PD-CATALYZED COUPLING REACTION OF ACETYLENES, IODOTRIMETHYLSILANE, AND ORGANOZINC REAGENTS FOR THE STEREOSELECTIVE SYNTHESIS OF VINYLSILANES [J].

CHATANI, N ;

AMISHIRO, N ;

MORII, T ;

YAMASHITA, T ;

MURAI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1834-1840

[7] A NEW CATALYTIC REACTION INVOLVING OXIDATIVE ADDITION OF IODOTRIMETHYLSILANE (ME3SII) TO PD(0) - SYNTHESIS OF STEREODEFINED ENYNES BY THE COUPLING OF ME3SII, ACETYLENES, AND ACETYLENIC TIN REAGENTS [J].

CHATANI, N ;

AMISHIRO, N ;

MURAI, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7778-7780

[8]

Christ- mann U, 2005, ANGEW CHEM, V117, P370

[9] Monoligated palladium species as catalysts in cross-coupling reactions [J].

Christmann, U ;

Vilar, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) :366-374

[10] Silicon-Based Cross-Coupling Reactions in the Total Synthesis of Natural Products [J].

Denmark, Scott E. ;

Liu, Jack H. -C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (17) :2978-2986

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