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Org Lett. 2005 Oct 13;7(21):4557-60.

Regioselectivity of Birch reductive alkylation of biaryls.

Author information

1
Université Bordeaux-I, Laboratoire de Chimie Organique et Organométallique, 351, Cours de la Libération, F-33405 Talence Cedex, France.

Abstract

[reaction: see text] 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.

PMID:
16209478
DOI:
10.1021/ol051377i
[Indexed for MEDLINE]

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