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

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 c...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2006-01 (13), p.1393-1394
Hauptverfasser: Clayden, Jonathan, Stimson, Christopher C, Keenan, Martine
Format: Artikel
Sprache:eng
Schlagworte:
Benzamides - chemistry
Molecular Structure
Sulfur - chemistry
Thiocarbamates - chemistry
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Zusammenfassung: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/b600181e