Regioselectivity of birch reductive alkylation of biaryls

被引：31

作者：

Lebeuf, R ^{[1
]}

Robert, F ^{[1
]}

Landals, Y ^{[1
]}

机构：

[1] Univ Bordeaux 1, Chim Organ & Organomet Lab, F-33405 Talence, France

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 21期

关键词：

D O I：

10.1021/ol051377i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselectivity of the Birch reductive alkylation of polysubstituted biaryls has been investigated. Results indicate that regioselectivity is affected by the electronic nature of substituents on both aromatic rings. The electron-rich 3,5-dimethoxyphenyl moiety is selectively reduced and then alkylated, while phenols and aniline are not dearomatized under these conditions. Biaryls possessing a phenol moiety are alkylated on the second ring, providing that the acidic proton has been removed prior to the Li/NH3 reduction.

引用

页码：4557 / 4560

页数：4

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