Journal
ORGANIC LETTERS
Volume 23, Issue 21, Pages 8327-8332Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03066
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Funding
- National Natural Science Foundation of China [21971182, 21771131]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
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This study presents a novel visible-light-initiated nickel-catalyzed O-arylation reaction of phenols with arylhalides, utilizing specific base and photosensitizer to achieve the reaction under visible light. The photocoupling reaction exhibits a broad substrate scope.
Notwithstanding some progress in nickel-catalyzed etherification of alkanols and arylhalides, the ability of such a Ni-catalyzed transformation employing phenols to diaryl ethers is unsuccessful due to phenolates with much lower reduction potentials, which suppress the oxidation of nickel(II) intermediates into requisite Ni(III) species. We herein report visible-light-initiated, nickel-catalyzed O-arylation of phenols with arylhalides using t-BuNH(i-Pr) as the base and thioxanthen-9-one as the photosensitizer under visible light. This photocoupling exhibits a broad substrate scope.
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