We
describe the development of a general palladium-catalyzed carbonylative
method to synthesize acyl fluorides from aryl, heteroaryl, alkyl,
and functionalized organic halides. Mechanistic analysis suggests
that the reaction proceeds via the synergistic combination
of visible light photoexcitation of Pd(0) to induce oxidative addition
with a ligand-favored reductive elimination. These together create
a unidirectional catalytic cycle that is uninhibited by the classical
effect of carbon monoxide coordination. Coupling the catalytic formation
of acyl fluorides with their subsequent nucleophilic reactions has
opened a method to perform carbonylation reactions with unprecedented
breadth, including the assembly of highly functionalized carbonyl-containing
products.
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