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