4.6 Article

Visible-Light-Induced Trifluoromethylation/Cyclization of 1,7-Enynes in Continuous Flow

Journal

ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 8, Issue 31, Pages 11729-11736

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.0c03745

Keywords

photoredox-catalyzed; trifluoromethylation; cyclization; 1,7-enynes; continuous-flow

Funding

  1. National Natural Science Foundation of China [21702103, 21522604, U1463201, 21402240]
  2. youth in Jiangsu Province Natural Science Fund [BK20150031, BK20130913, BY2014005-03]

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In the present study, we describe the successful development of a photoredox-catalyzed trifluoromethylation/cyclization of 1,7-enynes in a continuous-flow regime for the generation of several CF 3 -containing heterocyclic scaffolds. When using this protocol, a readily prepared Ph2SCF3OTf reagent was employed as the trifluoromethylation reagent, and various benzo[j]phenanthridines and indeno[1,2-c]quinolines were obtained in good to moderate yields. This transformation featured mild reaction conditions, a broad substrate scope, and ease of scale-up. Moreover, the continuous-flow processing in a photomicroreactor accelerated the reaction (5 min reaction time) and increased the product yields (up to 89%).

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