Work

Translation of Nickel-Catalyzed C(sp2)–C(sp3) Cross-Electrophile Coupling to Non-Amide Solvents

Year: 2025

Type: article

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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c01011

Authors: Brett D. Akana-Schneider, Julianna M. Mouat, Sisi Zhang, Michelle E. Akana, Bin Wu, Daniel J. Weix

Institution: University of Wisconsin–Madison

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green