Versatile Palladium-Catalyzed Approach to Acyl Fluorides and Carbonylations by Combining Visible Light- and Ligand-Driven Operations
journal contributionposted on 18.05.2022, 21:10 authored by Yi Liu, Cuihan Zhou, Meijing Jiang, Bruce A. Arndtsen
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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visible light photoexcitationsubsequent nucleophilic reactionsperform carbonylation reactionsmechanistic analysis suggestsinduce oxidative additionhighly functionalized carbonylfunctionalized organic halidesfavored reductive eliminationcombining visible lightcarbon monoxide coordinationunidirectional catalytic cyclesynthesize acyl fluoridescatalyzed carbonylative methodacyl fluoridescatalyzed approachcatalytic formationvia </versatile palladiumunprecedented breadthtogether createsynergistic combinationreaction proceedsgeneral palladiumdriven operationscontaining productsclassical effect