POLARITY-REVERSAL CATALYSIS BY THIOLS OF RADICAL-CHAIN HYDROSILYLATION OF ALKENES

被引：44

作者：

DANG, HS ^{[1
]}

ROBERTS, BP ^{[1
]}

机构：

[1] UCL, DEPT CHEM, CHRISTOPHER INGOLD LABS, LONDON WC1N 0AJ, ENGLAND

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 16期

关键词：

D O I：

10.1016/0040-4039(95)00372-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The radical-chain hydrosilylation of alkenes by triethylsilane under very mild conditions is promoted by thiols, which act as polnrity-reversal catalysts for the abstraction of electron-rich hydrogen from the silane by nucleophilic beta-silylalkyl radicals.

引用

页码：2875 / 2878

页数：4

共 20 条

[1] THIOLS AS POLARITY REVERSAL CATALYSTS FOR HYDROGEN-ATOM TRANSFER FROM ORGANOSILANES TO ALKYL RADICALS - REDUCTION OF ALKYL-HALIDES BY TRIETHYLSILANE [J].

ALLEN, RP ;

ROBERTS, BP ;

WILLIS, CR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (18) :1387-1388

[2]

BRUMWELL JE, 1994, TETRAHEDRON, V50, P13533

[3] ABSOLUTE RATE CONSTANTS FOR THE ADDITION OF TRIETHYLSILYL RADICALS TO VARIOUS UNSATURATED-COMPOUNDS [J].

CHATGILIALOGLU, C ;

INGOLD, KU ;

SCAIANO, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (10) :3292-3296

[4] RADICAL CHAIN REDUCTION OF ALKYL-HALIDES, DIALKYL SULFIDES AND O-ALKYL S-METHYL DITHIOCARBONATES TO ALKANES BY TRIALKYLSILANES [J].

COLE, SJ ;

KIRWAN, JN ;

ROBERTS, BP ;

WILLIS, CR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :103-112

[5]

Colvin E. W., 1981, SILICON ORGANIC SYNT

[6]

COLVIN EW, 1988, BEST SYNTHETIC METHO

[7] CATALYSIS OF HYDROSILYATION OF OLEFINS BY TERT-BUTYL PEROXIDE UNDER UV IRRADIATION [J].

EABORN, C ;

HARRISON, MR ;

WALTON, DRM .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 31 (01) :43-&

[8]

Eaborn C., 1968, ORGANOMETALLIC COM 1, V1

[9] FREE-RADICAL REACTIONS IN SOLUTION .8. RADICAL-INITIATED ADDITION OF TRIALKYLSILANES ACROSS ALKENE C=C BONDS [J].

ELDURINI, NMK ;

JACKSON, RA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 232 (02) :117-121

[10] FREE-RADICAL ADDITION TO OLEFINS OF AN H2S EQUIVALENT - TRIPHENYLSILANETHIOL [J].

HACHE, B ;

GAREAU, Y .

TETRAHEDRON LETTERS, 1994, 35 (12) :1837-1840

← 1 2 →