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Copper-catalyzed synthesis of trifluoromethylated bis(indolyl)arylmethanes from 2-arylindoles and 2,2,2-trifluoroacetohydrazide

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Abstract

One-pot synthesis of trifluoromethylated bis(indolyl)arylmethanes through copper-catalyzed reaction of 2-arylindoles with 2,2,2-trifluoroacetohydrazide is described. This viable transformation provides a variety of 3,3′-bis(indolyl)methanes with a CF3-containing tertiary carbon center in moderate to good yields. Preliminary mechanistic studies revealed that the reaction involves the in situ generation of a trifluoroacetyl radical and trapping with 2-arylindoles.

Graphical abstract: Copper-catalyzed synthesis of trifluoromethylated bis(indolyl)arylmethanes from 2-arylindoles and 2,2,2-trifluoroacetohydrazide

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Submitted
11 Sep 2019
Accepted
19 Dec 2019
First published
19 Dec 2019

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Copper-catalyzed synthesis of trifluoromethylated bis(indolyl)arylmethanes from 2-arylindoles and 2,2,2-trifluoroacetohydrazide

Z. Yuan, S. Chen and Z. Weng, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01131E

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