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

Author(s)
Maimone, Thomas; Kinzel, Tom; Zhang, Yong; Takase, Michael K.; Milner, Phillip John; ... Show more
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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.
Date issued
2011-10
URI
http://hdl.handle.net/1721.1/81966
Department
Massachusetts Institute of Technology. Department of Chemistry; Massachusetts Institute of Technology. Department of Materials Science and Engineering
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.
Version: Author's final manuscript
ISSN
0002-7863
1520-5126
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