title: 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. 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.
authors.affiliation: Department of Chemistry, Princeton University, 120 Washington Road, Princeton, NJ 08544 (USA).
authors.forename: Kevin M
authors.initials: KM
authors.lastname: Arendt
authors.affiliation: Department of Chemistry, Princeton University, 120 Washington Road, Princeton, NJ 08544 (USA). agdoyle@princeton.edu.
authors.forename: Abigail G
authors.initials: AG
authors.lastname: Doyle
mesh_terms: D000080:Acetals / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D000080:Acetals; D004987:Ethers; D006847:Hydrocarbons, Iodinated; D009942:Organometallic Compounds; D009532:Nickel
keywords: cross-coupling; ethers; nickel; radicals; synthetic methods