Evidence for in Situ Catalyst Modification during the Pd-Catalyzed Conversion of Aryl Triflates to Aryl Fluorides
Journal of the American Chemical Society2011Vol. 133(45), pp. 18106–18109
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Thomas J. Maimone, Phillip J. Milner, Tom Kinzel, Yong Zhang, Michael K. Takase, Stephen L. Buchwald
Abstract
A mechanistic investigation of the Pd-catalyzed conversion of aryl triflates to fluorides is presented. Studies reveal that C-F reductive elimination from a LPd(II)(aryl)F complex (L = t-BuBrettPhos or RockPhos) does not occur when the aryl group is electron rich. Evidence is presented that a modified phosphine, generated in situ, serves as the actual supporting ligand during catalysis with such substrates. A preliminary study of the reactivity of a LPd(II)(aryl)F complex based on this modified ligand is reported.
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