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Arylphosphonylation and Arylazidation of Activated Alkenes
Author(s) -
Kong Wangqing,
Merino Estíbaliz,
Nevado Cristina
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201311241
Subject(s) - substituent , stereocenter , regioselectivity , aryl , chemistry , nitrogen atom , alkyl , carbon atom , nitrogen , medicinal chemistry , organic chemistry , catalysis , enantioselective synthesis
Two radical‐mediated processes of activated alkenes, namely arylphosphonylation and arylazidation, are described. The difunctionalization of alkenes by a tandem process that involves radical addition, 1,4‐aryl migration, and desulfonylation generates α‐aryl‐β‐heterofunctionalized amides bearing a quaternary stereocenter when the substituent on the nitrogen atom is an aryl group. Alternatively, heterooxindoles or spirobicycles can be obtained with excellent regioselectivity in the presence of an alkyl substituent on the nitrogen atom.