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Regioselectivity of Birch reductive alkylation of biaryls



Regioselectivity of Birch reductive alkylation of biaryls



Organic Letters 7(21): 4557-4560



[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.

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Accession: 050148753

Download citation: RISBibTeXText

PMID: 16209478

DOI: 10.1021/ol051377i


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