Difluoroalkylation/C–H Annulation Cascade Reaction Induced by Visible-Light Photoredox Catalysis

We report the first example of difluoroalkylation/​C–H annulation cascade reactions of cyclopropyl olefins induced by visible-light photoredox catalysis regioselectively affording partially hydrogenated naphthalenes and quinolines with a variety of difluorinated side chains. The alkylation reagent c...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-10, Vol.81 (20), p.9992-10001
Main Authors: Li, Jin, Chen, Jingzhi, Jiao, Wei, Wang, Guoqiang, Li, Ying, Cheng, Xu, Li, Guigen
Format: Article
Language:English
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Summary:We report the first example of difluoroalkylation/​C–H annulation cascade reactions of cyclopropyl olefins induced by visible-light photoredox catalysis regioselectively affording partially hydrogenated naphthalenes and quinolines with a variety of difluorinated side chains. The alkylation reagent could be extended to monofluoro and trifluoro reagents, nitrile and malonate. The regioselectivity was investigated by means of density functional theory calculations.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01825