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Dialkyl Ether Formation by Nickel‐Catalyzed Cross‐Coupling of Acetals and Aryl Iodides
Author(s) -
Arendt Kevin M.,
Doyle Abigail G.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503936
Subject(s) - aryl , catalysis , chemistry , nickel , ether , pyridine , catalytic cycle , substrate (aquarium) , coupling reaction , combinatorial chemistry , radical , medicinal chemistry , organic chemistry , polymer chemistry , alkyl , oceanography , geology
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 CC bond‐forming approach to dialkyl ether synthesis. Characterization of a [(bpp)NiCl] complex relevant to the proposed catalytic cycle is also described.