Journal
ORGANIC LETTERS
Volume 22, Issue 14, Pages 5369-5374Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01668
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Funding
- National Institutes of Health [R35-GM122483]
- Arnold and Mabel Beckman Foundation
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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.
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