Intramolecular Fe(II)-Catalyzed N-O or N-N Bond Formation from Aryl Azides

被引：182

作者：

Stokes, Benjamin J. ^{[1
]}

Vogel, Carl V. ^{[1
]}

Urnezis, Linda K. ^{[1
]}

Pan, Minjie ^{[1
]}

Driver, Tom G. ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 12期

基金：

美国国家卫生研究院;

关键词：

AQUEOUS HYDROGEN-PEROXIDE; ORGANIC AZIDES; ASYMMETRIC OXIDATION; NITRO-COMPOUNDS; SULFIDES; COMPLEXES; REARRANGEMENT; SULFIMIDATION; SULFOXIDES; EFFICIENT;

D O I：

10.1021/ol101040p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents Into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates a variety of different functional groups to facilitate access to a range of benzisoxazoles or indazoles. The unreactivity of the Z-methyloxime indicates that N-heterocycle formation occurs through a nucleophilic attack of the ketone or oxime onto an activated planar iron azide complex.

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页码：2884 / 2887

页数：4

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