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Visible Light Photoredox Catalyzed Cascade Cyclizations of α‐Bromochalcones or α‐Bromocinnamates with Heteroarenes
Author(s) -
Paria Suva,
Reiser Oliver
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201301069
Subject(s) - chemistry , photoredox catalysis , iridium , radical , catalysis , photochemistry , quenching (fluorescence) , visible spectrum , cascade , combinatorial chemistry , photocatalysis , organic chemistry , fluorescence , quantum mechanics , physics , optoelectronics , chromatography
Vinyl radicals were generated from α‐bromochalcones or α‐bromocinnamate ethyl ester under visible light photoredox catalyzed conditions via an oxidative quenching cycle of the iridium complex [Ir{dF(CF 3 )ppy} 2 (dtbbpy)]PF 6 and subjected to cascade cyclizations with heteroarenes entailing two consecutive CC bond formations and three CH activations. The process is amenable to furans, benzofurans, pyrroles, and indoles, giving rise to a broad variety of novel polycyclic frameworks in high yields under mild and environmentally benign reaction conditions.