Monofluoroalkenes are stable and lipophilic amide bioisosteres used in medicinal chemistry. However, efficient and stereoselective methods for synthesizing -monofluoroalkenes are underdeveloped. We envisage β-fluoro-vinyl iodonium salts (-FVIs) as coupling partners for the diverse and stereoselective synthesis of -monofluoroalkenes. Disclosed herein is the development and application of a silver(I)-catalyzed process for accessing a broad scope of ()-FVIs with exclusive -stereoselectivity and regioselectivity from alkynes in a single step. Experimental and computational studies provide insight into the mechanism of the catalytic cycle and the role of the silver(I) catalyst, and the reactivity of ()-FVIs is explored through several stereospecific derivatizations.
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| http://dx.doi.org/10.1021/jacs.4c03826 | DOI Listing |
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