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. 2006 Apr 7:(13):1393-4.
doi: 10.1039/b600181e. Epub 2006 Feb 21.

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

Jonathan Clayden  1 , Christopher C Stimson, Martine Keenan
Affiliations

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

Jonathan Clayden et al. Chem Commun (Camb). .

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.

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