Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation.
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.
Clayden
Jonathan
J
School of Chemistry, University of Manchester, Oxford Road, Manchester, UKM13 9PL. clayden@man.ac.uk
Stimson
Christopher C
CC
Keenan
Martine
M
D001549:Benzamides / Q000737:chemistry; D015394:Molecular Structure; D013455:Sulfur / Q000737:chemistry*; D013859:Thiocarbamates / Q000737:chemistry*
D001549:Benzamides; D013859:Thiocarbamates; C023898:butylate; D013455:Sulfur