Evidence for in Situ Catalyst Modification during the Pd-Catalyzed Conversion of Aryl Triflates to Aryl Fluorides
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Buchwald_Evidence for in situ.pdf
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Author(s)
Maimone, Thomas
Kinzel, Tom
Zhang, Yong
Takase, Michael K.
Milner, Phillip John
Buchwald, Stephen Leffler
Date Issued
October 2011
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Maimone, Thomas J., Phillip J. Milner, Tom Kinzel, Yong Zhang, Michael K. Takase, and Stephen L. Buchwald. “Evidence for in Situ Catalyst Modification during the Pd-Catalyzed Conversion of Aryl Triflates to Aryl Fluorides.” Journal of the American Chemical Society 133, no. 45 (November 16, 2011): 18106-18109.
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Author's final manuscript
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[superscript 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[superscript II](aryl)F complex based on this modified ligand is reported.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Massachusetts Institute of Technology. Department of Materials Science and Engineering
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DOI of Published Version
https://doi.org/10.1021/ja208461k
