期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 44, 页码 12923-12927出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505550
关键词
alkenes; alkynes; fluorine; photocatalysis; trifluoromethylation
资金
- JSPS (KAKENHI) [26288045, 15K13689, 15J12072]
- Naito Foundation
- Grants-in-Aid for Scientific Research [26288045, 15K13689, 15J12072] Funding Source: KAKEN
A regio- and stereoselective synthesis of trifluoromethylated alkenes bearing four different substituents has been developed. Stereocontrolled sulfonyloxytrifluoromethylation of unsymmetric internal alkynes with an electrophilic CF3 reagent, namely the triflate salt of the Yagupol'skii-Umemoto reagent, in the presence of an Ir photoredox catalyst under visible-light irradiation afforded trifluoromethylalkenyl triflates with well-predictable stereochemistry resulting from antiaddition of the trifluoromethyl and triflate groups. Subsequent palladium-catalyzed cross-couplings led to tetrasubstituted trifluoromethylated alkenes in a highly stereoselective manner. The present method is the first example of a facile one-pot synthesis of tetrasubstituted trifluoromethylated alkenes from simple alkynes.
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