In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides
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Buchwald_In-depth assessment.pdf
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Author(s)
Milner, Phillip John
Yang, Yang
Buchwald, Stephen Leffler
Date Issued
August 2015
Journal
Organometallics
Publisher
American Chemical Society (ACS)
Citation
Milner, Phillip J., Yang Yang, and Stephen L. Buchwald. “In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides.” Organometallics 34.19 (2015): 4775–4780. © 2015 American Chemical Society
Version
Final published version
Abstract
A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C–F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/acs.organomet.5b00631
