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Issue 13, 2006
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Contra-Friedel–Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation

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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.

Graphical abstract: Contra-Friedel–Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation

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Supplementary files

Article information


Submitted
06 Jan 2006
Accepted
02 Feb 2006
First published
21 Feb 2006

Chem. Commun., 2006, 1393-1394
Article type
Communication

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

J. Clayden, C. C. Stimson and M. Keenan, Chem. Commun., 2006, 1393
DOI: 10.1039/B600181E

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