Catalyst-free and selective trifluoromethylative cyclization of acryloanilides using PhICFCl.

Org Biomol Chem

Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, College of Chemistry, Northeast Normal University, 5268 Renmin Street, Changchun, China.

Published: May 2019

Trifluoromethylation-triggered cyclization of alkenes provides a useful route to CF3-containing cyclic compounds. Current approaches to generate CF3-based initiators from a CF3 source require a catalyst or an activator. This work describes a catalyst-free protocol to innately produce electrophilic CF3 species from PhICF3Cl for trifluoromethylative cyclization of acryloanilides. A new domino biscyclization of dienes has been developed leading to trifluoroethylated tetrahydroindenoquinolinones with chemo- and stereo-selectivity.

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http://dx.doi.org/10.1039/c9ob00601jDOI Listing

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