Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 28, Pages 11293-11297Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202002219
Keywords
C-F bonds; fluoroalkenes; fluoroenynes; oxidative addition; palladium
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Funding
- Research Grants Council of Hong Kong [CUHK 24301217]
- Chinese University of Hong Kong
- Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
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A stereoselective Pd(PPh3)(4)-catalyzed C-F bond alkynylation of tetrasubstituted gem-difluoroalkenes with terminal alkynes has been developed. This method gives access to a great variety of conjugated monofluoroenynes bearing a tetrasubstituted alkene moiety with well-defined stereochemistry. Chelation-assisted oxidative addition of Pd to the C-F bond is proposed to account for the high level of stereocontrol. An X-ray crystal structure of a key monofluorovinyl Pd-II intermediate has been obtained for the first time as evidence for the proposed mechanism.
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