Improved Process for the Palladium-Catalyzed C–O Cross-Coupling of Secondary Alcohols
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nihms-1679392.pdf
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Accepted version
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1.52 MB
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Author(s)
Zhang, Hong
Ruiz-Castillo, Paula
Schuppe, Alexander W.
Buchwald, Stephen L.
Date Issued
June 2020
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Zhang, Hong, Ruiz-Castillo, Paula, Schuppe, Alexander W and Buchwald, Stephen L. 2020. "Improved Process for the Palladium-Catalyzed C–O Cross-Coupling of Secondary Alcohols." Organic Letters, 22 (14).
Version
Author's final manuscript
Abstract
Copyright © 2020 American Chemical Society. An improved protocol for the Pd-catalyzed C-O cross-coupling of secondary alcohols is described. The use of biaryl phosphine L2 as the ligand was key to achieving efficient cross-coupling of (hetero)aryl chlorides with only a 20% molar excess of the alcohol. Additionally, we observed an unusual reactivity difference between an electron-rich aryl bromide and the analogous aryl chloride, and deuterium-labeling suggested that currently unidentified pathways for reduction play an important role in explaining this disparity.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1021/acs.orglett.0c01668
