Chemical Communications 2006-04-07

Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation.

Jonathan Clayden, Christopher C Stimson, Martine Keenan

Index: Chem. Commun. (Camb.) (13) , 1393-4, (2006)

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Abstract

Directed metallation and sulfinylation yields sulfoxides which undergo ipso nucleophilic aromatic substitution with tertiary and secondary alkyllithiums, giving aromatic rings bearing alkyl groups generally incompatible with directed metallation methods and with regioselectivity complementary with classical Friedel-Crafts substitution.