Electrochemical Strategy for the Radical Fluoroacetylation of Sulfoximines from Fluorinated Alkyl Carboxylic Acids

The integration of trifluoroacetyl (CF3CO) groups into organic skeletons is a key research topic in synthetic chemistry given their significant potential to boost biological activity. Despite recent developments of strategies for incorporating trifluoroacetyl moiety via trifluoroacetyl radical intermediates, the practical utilization of inexpensive and readily available trifluoroacetic acids as trifluoroacetyl radical sources has not yet been developed. Herein, an electrochemical strategy has been employed to achieve the radical deoxygenative transformation of trifluoroacetic acids directly with the assistance of PPh3. The obtained trifluoroacetyl radicals are then coupled with sulfoximine species, thus enabling the synthesis of N-trifluoroacetylated sulfoximines. Additionally, other fluorinated alkyl carboxylic acids, including perfluoro-, difluoro-, and trifluoromethylcarboxylic acids, can also be efficiently utilized under these conditions, leading to their corresponding acylated sulfoximines. Moreover, the trifluoroacetylation of drug-based molecules and the easy execution of scale-up experiments highlight the applicability of this protocol.