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Visible Light‐Mediated Coupling of α‐Bromochalcones with Alkenes
Author(s) -
Paria Suva,
Kais Viktor,
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.201400638
Subject(s) - chemistry , alkene , allylic rearrangement , iridium , steric effects , radical , intermolecular force , photochemistry , coupling (piping) , photocatalysis , photoredox catalysis , heck reaction , catalysis , palladium , stereochemistry , organic chemistry , molecule , mechanical engineering , engineering
Photoredox catalyzed intermolecular couplings of α‐bromochalcones to olefins have been developed. Employing 1 mol% of the iridium complex Ir(ppy) 3 as photocatalyst, vinyl radicals are generated from α‐bromochalcones as the key intermediate, which efficiently engage in a formal [4+2] cyclization with various alkenes. The resulting 3,4‐dihydronaphthalenes can be readily transformed to the corresponding naphthalenes and further cyclized to 5 H ‐benzo[ c ]fluorenes. Alternatively, Heck‐type coupling products are obtained with sterically more hindered alkenes or allylated products if the alkene possesses a suitable leaving group in the allylic position.