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Highly Selective Three‐Component Coupling of Ethyl Propiolate, Alkenes, and Diphenyl Diselenide under Visible‐Light Irradiation
Author(s) -
Ogawa Akiya,
Doi Mikio,
Ogawa Ikuko,
Hirao Toshikazu
Publication year - 1999
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/(sici)1521-3773(19990712)38:13/14<2027::aid-anie2027>3.0.co;2-m
Subject(s) - alkene , alkyne , diphenyl diselenide , photochemistry , coupling (piping) , chemistry , irradiation , diselenide , component (thermodynamics) , medicinal chemistry , polymer chemistry , organic chemistry , materials science , catalysis , physics , selenium , nuclear physics , metallurgy , thermodynamics
Just the right strength of carbon‐radical trapping by diphenyl diselenide facilitates its selective three‐component coupling with an electron‐poor alkyne and an electron‐rich alkene [Eq. (1)]. In contrast, (PhS) 2 is too weak and (PhTe) 2 too strong a radical trap, and polymerization of the unsaturated compounds and addition of (PhTe) 2 to the alkyne occur, respectively.