Studying Regioisomer Formation in the Pd-Catalyzed Fluorination of Aryl Triflates by Deuterium Labeling
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Buchwald_Studying regioisomer.pdf
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2.17 MB
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Author(s)
Milner, Phillip John
Kinzel, Tom
Zhang, Yong
Buchwald, Stephen Leffler
Date Issued
October 2014
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Milner, Phillip J., Tom Kinzel, Yong Zhang, and Stephen L. Buchwald. “Studying Regioisomer Formation in the Pd-Catalyzed Fluorination of Aryl Triflates by Deuterium Labeling.” Journal of the American Chemical Society 136, no. 44 (November 5, 2014): 15757–15766. © 2014 American Chemical Society
Version
Final published version
Abstract
Isotopic labeling has been used to determine that a portion of the desired product in the Pd-catalyzed fluorination of electron-rich, non-ortho-substituted aryl triflates results from direct C–F cross-coupling. In some cases, formation of a Pd-aryne intermediate is responsible for producing undesired regioisomers. The generation of the Pd-aryne intermediate occurs primarily via ortho-deprotonation of a L·Pd(Ar)OTf (L = biaryl monophosphine) species by CsF and thus competes directly with the transmetalation step of the catalytic cycle. Deuterium labeling studies were conducted with a variety of aryl triflates.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja509144r
