Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds

Autor: Gerold Heuger, Richard Göttlich
Jazyk: angličtina
Rok vydání: 2015
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 11, Iss 1, Pp 1226-1234 (2015)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.11.136
Popis: N-Alkyl-N-chlorosulfonamides add to alkenes under copper(I) catalysis. In reactions of styrene derivatives with terminal double bonds the addition products were obtained in excellent yield and high regioselectivity. Lower yields are obtained in addition reactions to non-aromatic alkenes. The reaction most likely proceeds via a redox catalysis and amidyl radicals, a concerted mechanism has been ruled out and a polar mechanism via chloronium ions would lead to the opposite regiochemistry.
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