Tin-free radical reactions mediated by organoboron compounds

被引：74

作者：

Darmency, Vincent ^{[1
]}

Renaud, Philippe ^{[1
]}

机构：

[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland

来源：

RADICALS IN SYNTHESIS I: METHODS AND MECHANISMS | 2006年 / 263卷

关键词：

atom transfer reactions; boron; C-C bond formation; conjugate addition; radical initiators; radical reaction; tin-free;

D O I：

10.1007/128_030

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of tin-free methods to run radical reactions is crucial for their applications in industrial processes as well as in drug discovery projects. Within the last 10 years, organoboron compounds have demonstrated that they represent one of the most attractive approach to substitute tin reagents in radical process. This review summarizes the results obtained with organoboron compounds as a source of alkyl radicals. Four different strategies are described, i.e., the use of organoboranes as radical initiators, as a source of alkyl radicals, as chain transfer reagents, and finally as reducing agents.

引用

页码：71 / 106

页数：36

共 132 条

[1] STEREOCONTROLLED CONSTRUCTION OF 6 BULLET 5 BULLET 6 AND 5 BULLET 5 BULLET 6 RING-SYSTEMS BY RADICAL TANDEM CYCLIZATION [J].

ALBRECHT, U ;

WARTCHOW, R ;

HOFFMANN, HMR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (07) :910-913

[2]

Alves MJ, 2003, SYNLETT, P1403

[3]

ATTANASI O, 1973, GAZZ CHIM ITAL, V103, P31

[4] ELECTRON-SPIN-RESONANCE STUDIES OF RADICALS DERIVED FROM 1,3,2-BENZODIOXABOROLES [J].

BABAN, JA ;

GOODCHILD, NJ ;

ROBERTS, BP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (01) :157-161

[5] SYNTHESIS OF GAMMA-HALOESTERS AND GAMMA-KETOESTERS BY HOMOLYTIC ADDITION OF CARBON RADICALS GENERATED BY ALPHA-HALOESTERS AND TRIETHYLBORANE TO ALKENES AND SILYL ENOL ETHERS [J].

BACIOCCHI, E ;

MURAGLIA, E .

TETRAHEDRON LETTERS, 1994, 35 (17) :2763-2766

[6] ON THE STABILITY AND RADICAL DEOXYGENATION OF TERTIARY XANTHATES [J].

BARTON, DHR ;

PAREKH, SI ;

TSE, CL .

TETRAHEDRON LETTERS, 1993, 34 (17) :2733-2736

[7]

Batey RA, 1999, ANGEW CHEM INT EDIT, V38, P1798, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1798::AID-ANIE1798>3.0.CO

[8]

2-0

[9]

Becattini B, 2003, SYNLETT, P1485

[10] DIASTEREOSELECTIVE FORMATION OF CYCLIC CARBONATES BY CYCLIZATION OF ALKENYLOXYCARBONYLOXY RADICALS [J].

BECKWITH, ALJ ;

DAVISON, IGE .

TETRAHEDRON LETTERS, 1991, 32 (01) :49-52

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