Synthesis using aromatic homolytic substitution - recent advances

被引：265

作者：

Bowman, W. Russell ^{[1
]}

Storey, John M. D.

机构：

[1] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England

[2] Univ Aberdeen, Dept Chem, Old Aberdeen AB24 3UE, Scotland

来源：

CHEMICAL SOCIETY REVIEWS | 2007年 / 36卷 / 11期

关键词：

D O I：

10.1039/b605183a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This critical review aims at presenting recent developments in intramolecular aromatic homolytic substitution which has become one of the common methodologies in modern synthesis. The application of Bu3SnH- mediated cyclisations have proved especially useful. The critical review illustrates the mechanistic considerations required for planning synthetic applications and a wide range of synthetic protocols and natural product syntheses are shown. The latest evidence for the mechanisms involved in aromatic homolytic substitution are presented. ( 152 references).

引用

页码：1803 / 1822

页数：20

共 216 条

[1]

ALBAN MA, 2006, ORG LETT, V8, P3513

[2] Synthesis of fused or not β-lactam-biaryl hybrids by free radical aryl-aryl coupling of 2-azetidinone-tethered haloarenes [J].

Alcaide, B ;

Almendros, P ;

Pardo, C ;

Rodríguez-Vicente, A ;

Ruiz, MP .

TETRAHEDRON, 2005, 61 (33) :7894-7906

[3] New intramolecular cyclization and rearrangement processes based on the radical aryl-aryl coupling of arylsubstituted 2-azetidinones [J].

Alcaide, B ;

Rodríguez-Vicente, A .

TETRAHEDRON LETTERS, 1998, 39 (36) :6589-6592

[4] Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles [J].

Aldabbagh, F ;

Bowman, WR ;

Mann, E ;

Slawin, AMZ .

TETRAHEDRON, 1999, 55 (26) :8111-8128

[5] Synthesis of heterocycles by radical cyclisation [J].

Aldabbagh, F ;

Bowman, WR .

CONTEMPORARY ORGANIC SYNTHESIS, 1997, 4 (04) :261-280

[6] Radical cyclisation onto imidazoles and benzimidazoles [J].

Aldabbagh, F ;

Bowman, WR .

TETRAHEDRON, 1999, 55 (13) :4109-4122

[7] Oxidative radical cyclisations onto imidazoles and pyrroles using Bu3SnH [J].

Aldabbagh, F ;

Bowman, WR ;

Mann, E .

TETRAHEDRON LETTERS, 1997, 38 (45) :7937-7940

[8] Radical cyclisation onto imidazoles and benzimidazoles [J].

Aldabbagh, F ;

Bowman, WR .

TETRAHEDRON LETTERS, 1997, 38 (21) :3793-3794

[9] Intramolecular aromatic substitutions of the imidazol-5-yl radical to form tricyclic imidazo[5,1-a] heterocycles [J].

Aldabbagh, Fawaz ;

Clyne, Mairead A. .

LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (07) :510-513

[10] Aromatic homolytic substitution using solid phase synthesis [J].

Allin, SM ;

Bowman, WR ;

Karim, R ;

Rahman, SS .

TETRAHEDRON, 2006, 62 (18) :4306-4316

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