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Updated: Apr 6, 2026
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Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides
Kevin M Arendt1, Abigail G Doyle2
1Department of Chemistry, Princeton University, 120 Washington Road, Princeton, NJ 08544 (USA).
Abstract:
A new substrate class for nickel-catalyzed C(sp(3)) cross-coupling reactions is reported. α-Oxy radicals generated from benzylic acetals, TMSCl, and a mild reductant can participate in chemoselective cross-coupling with aryl iodides using a 2,6-bis(N-pyrazolyl)pyridine (bpp)/Ni catalyst. The mild, base-free conditions are tolerant of a variety of functional groups on both partners, thus representing an attractive C-C bond-forming approach to dialkyl ether synthesis. Characterization of a [(bpp)NiCl] complex relevant to the proposed catalytic cycle is also described.
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