Direct C(sp³)-H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals

Benjamin J. Shields and Abigail G. Doyle*

*Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States, Email: agdoyleprinceton.edu

B. J. Shields, A. G. Doyle, J. Am. Chem. Soc., 2016, 138, 12719-12722.

DOI: 10.1021/jacs.6b08397

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Abstract

In a Ni-catalyzed photoredox reaction, aryl chlorides serve as both cross-coupling partners and the chlorine radical source for the α-oxy C(sp³)-H arylation of cyclic and acyclic ethers. Photolysis of a Ni(III) aryl chloride intermediate, generated by photoredox-mediated single-electron oxidation, leads to elimination of a chlorine radical.

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Key Words

tetrahydrofurans

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ID: J48-Y2016