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The unprecedented synthesis of gem-difluoroalkenes through the Ramberg-Bäcklund reaction of alkyl triflones is described herein. Structurally diverse, fully-substituted gem-difluoroalkenes that are difficult to prepare by other methods can be easily… Click to show full abstract
The unprecedented synthesis of gem-difluoroalkenes through the Ramberg-Bäcklund reaction of alkyl triflones is described herein. Structurally diverse, fully-substituted gem-difluoroalkenes that are difficult to prepare by other methods can be easily prepared from readily available triflones by treatment with specific Grignard reagents. Experimental and computational studies provide insight into the unique and critical role of Grignard reagent, which serves both as a base to remove the alpha-proton, and as a Lewis acid to assist C-F bond activation.
Journal Title: Journal of the American Chemical Society
Year Published: 2020
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