Domino cyclization/trifluoromethylation of 2-alkynylanilines using fluoroform-derived CuCF3: synthesis of 3-(trifluoromethyl)indoles

By employing easily accessible 2-alkynylanilines and the well-established fluoroform-derived CuCF3 reagent, a novel class of 3-(trifluoromethyl)indoles can be synthesized in good yields with no ambiguity of the CF3 position. The method utilizes a domino cyclization/trifluoromethylation strategy to c...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2018, Vol.5 (9), p.1511-1515
Main Authors: Ye, Yibin, Kelvin Pak Shing Cheung, He, Lisi, Gavin Chit Tsui
Format: Article
Language:English
Subjects:
Indoles
Organic chemistry
Reagents
Trifluoromethane
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Summary:By employing easily accessible 2-alkynylanilines and the well-established fluoroform-derived CuCF3 reagent, a novel class of 3-(trifluoromethyl)indoles can be synthesized in good yields with no ambiguity of the CF3 position. The method utilizes a domino cyclization/trifluoromethylation strategy to construct the indole cores with the concomitant installation of the CF3 group. The ultimate source of CF3 is the low-cost industrial by-product fluoroform (CF3H).
ISSN:2052-4110
2052-4110
DOI:10.1039/c8qo00191j