Translation of Nickel-Catalyzed C(sp2)-C(sp3) Cross-Electrophile Coupling to Non-Amide Solvents
Brett D Akana-Schneider1, Julianna M Mouat1, Sisi Zhang2
1Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
Abstract:
The cross-electrophile coupling of organobromides is widely utilized in organic synthesis but generally requires undesirable amide solvents (e.g., DMF, DMA, and NMP). We report that the combination of a strongly donating, bidentate nitrogen ligand, LiI, and 4-picoline enables coupling in a variety of alcohol, ester, and ethereal solvents at up to 50 g scale. An improved synthesis of the optimal ligand, 4,4'-bis(dimethylamino)-2,2'-bipyridine, is also reported on the basis of the reductive homocoupling of 4-dimethylamino-2-chloropyridine.
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