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Evidence for in Situ Catalyst Modification during the Pd-Catalyzed Conversion of Aryl Triflates to Aryl Fluorides

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journal contribution
posted on 16.11.2011, 00:00 by Thomas J. Maimone, Phillip J. Milner, Tom Kinzel, Yong Zhang, Michael K. Takase, Stephen L. Buchwald
A mechanistic investigation of the Pd-catalyzed conversion of aryl triflates to fluorides is presented. Studies reveal that C–F reductive elimination from a LPdII(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 LPdII(aryl)F complex based on this modified ligand is reported.

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