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

Brett D, Akana-Schneider, Julianna M, Mouat, Zhang, Sisi, Michelle, Akana, Wu, Bin-3 and Daniel J, Weix (2025) Translation of Nickel-Catalyzed C(sp2)-C(sp3) Cross-Electrophile Coupling to Non-Amide Solvents. Organic Letters. ISSN 1523-70601523-7052

Abstract

he cross-electrophile coupling of organobromides iswidely utilized in organic synthesis but generally requires undesirableamide solvents (e.g., DMF, DMA, and NMP). We report that thecombination of a strongly donating, bidentate nitrogen ligand, LiI, and4-picoline enables coupling in a variety of alcohol, ester, and etherealsolvents at up to 50 g scale. An improved synthesis of the optimalligand, 4,4′-bis(dimethylamino)-2,2′-bipyridine, is also reported on thebasis of the reductive homocoupling of 4-dimethylamino-2-chloropyridine

Item Type: Article
Date Deposited: 29 Apr 2025 00:45
Last Modified: 29 Apr 2025 00:45
URI: https://oak.novartis.com/id/eprint/56218

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