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Stereoselective Synthesis of Highly Functionalized Indanes and Dibenzocycloheptadienes through Complex Radical Cascade Reactions
Author(s) -
Kong Wangqing,
Fuentes Noelia,
GarcíaDomínguez Andres,
Merino Estíbaliz,
Nevado Cristina
Publication year - 2015
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.201409659
Subject(s) - stereoselectivity , radical , chemistry , aryl , styrene , free radical reaction , radical cyclization , aryl radical , cascade , ring (chemistry) , combinatorial chemistry , polymer chemistry , organic chemistry , catalysis , polymer , alkyl , chromatography , copolymer
Two highly stereoselective radical‐mediated syntheses of densely functionalized indanes and dibenzocycloheptadienes from ortho ‐vinyl‐ and ortho ‐vinylaryl‐substituted N ‐(arylsulfonyl)‐acrylamides, respectively, are presented here. The chemoselective addition of in situ generated radicals (X . ) onto the styrene moieties triggers an unprecedented reaction cascade, resulting in the formation of one new CX bond and two new CC bonds, a formal 1,4‐aryl migration, and the extrusion of SO 2 to generate an amidyl radical intermediate. This intermediate, upon H abstraction, leads to the observed 5‐ and 7‐membered ring carbocyclic products, respectively, in a highly efficient manner.