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Highly Selective Sequential Addition and Cyclization Reactions Involving Diphenyl Diselenide, an Alkyne, and Alkenes under Visible‐Light Irradiation
Author(s) -
Tsuchii Kaname,
Doi Mikio,
Hirao Toshikazu,
Ogawa Akiya
Publication year - 2003
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.200250790
Subject(s) - diselenide , diphenyl diselenide , alkyne , chemistry , photochemistry , medicinal chemistry , organic chemistry , catalysis , selenium
A four‐component radical coupling of diphenyl diselenide, an alkyne, and two olefins to form substituted cyclopentanes in good yields is described (see scheme). This selective sequential addition and cyclization is facilitated by the rate of carbon‐radical trapping by diphenyl diselenide, appropriate for this transformation, and the efficiency of the 5‐ exo cyclization. EWG=electron‐withdrawing group.