Cooperative Trifluoromethyl Group and Catalyst-Enabled Regioselective 3,4-fuctionalization of Unsymmetric β-CF3-1,3-enynes via C-H Bond Activation

28 March 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

1-isoquinolin-1(2H)-one skeleton exists widely in natural products, pharmaceuticals and materials. We disclose here a fluorine effect and catalyst cooperatively induced regioselective or regiospecific 3,4-functionalization of unsymmetric 2-CF3-1,3-enynes. The presence of trifluoromethyl group is determinable for the regioselectivity. When the CF3 group were replaced with the methyl, amide group, the regioselectivity decreased to a ratio of 1.3:1 or 1:1.7. For alkyl substituted β-CF3-1,3-enynes, a regiospecificity was obtained. This strategy features excellent regioselectivity, broad substrate scope and high functional group tolerance. Mechanistic studies showed C-H bond activation is the rate-limiting step.

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Supporting information
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all the experiments, procedure, X-ray data and NMR spectra were included
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