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 inJournal of organic chemistry Vol. 81; no. 20; pp. 9992 - 10001
Main Authors Li, Jin, Chen, Jingzhi, Jiao, Wei, Wang, Guoqiang, Li, Ying, Cheng, Xu, Li, Guigen
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.10.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HYDRAZONES
ALKENES
HETEROARENES
DIFLUOROMETHYL
5+1 CYCLOADDITION
VINYLCYCLOPROPANES
FLUORINE
ALPHA
PERFLUOROALKYLATION
TRIFLUOROMETHYLATION
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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.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01825