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Article Abstract
A mild and chemoselective method for the thioacylation of amines, including amino acids and peptides, using -difluoroalkenes and sulfide, is reported. The distinguishing of the different nucleophilic sites (-site and diverse -sites) by the chemoselective C-F bond functionalization of -difluoroalkenes enables the unique synergistic defluorinative coupling reaction. This reaction features mild conditions, is operationally simple, efficient, and gram-scalable, tolerates various functional groups, and is activator-free and without racemization. Thioamide moieties were incorporated site-specifically into bioactive compounds. The proposed mechanism is illustrated by a DFT calculation.
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| http://dx.doi.org/10.1021/acs.orglett.4c02237 | DOI Listing |
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