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Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides.

ABSTRACT: A new substrate class for nickel-catalyzed C(sp(3)) cross-coupling reactions is reported. ?-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.

SUBMITTER: Arendt KM

PROVIDER: S-EPMC4629785 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides.

Arendt Kevin M KM Doyle Abigail G AG

Angewandte Chemie (International ed. in English) 20150715 34

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)N ...[more]

PMID: 26219537

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