The
catalyst-free electrochemical di- and trifluoromethylation/cyclization
of N-substituted acrylamides was realized under external oxidant-free
conditions. The strategy provides expedient access to fluoroalkylated
oxindoles and 3,4-dihydroquinolin-2(1H)-ones with
ample scope and broad functional group tolerance by mild, direct electrolysis
of sodium sulfinates in an undivided cell. Detailed mechanistic studies
provided strong support for a SET-based reaction manifold.
Expanding ring under green electricity: The electrosynthetic approach enabled atom-economical synthesis of challenging medium-sized lactams through a unique remote amidyl migration under exceedingly mild, transition metal- and oxidant-free conditions.
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