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

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-14 DOI:10.1021/acs.orglett.5c01011

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

引用次数: 0

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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将镍催化的 C(sp2)-C(sp3)交电偶联转化为非酰胺类溶剂

有机溴化物的交叉亲电偶联广泛应用于有机合成，但通常需要不良的酰胺溶剂（如DMF， DMA和NMP）。我们报道了一种强供体，双齿氮配体，LiI和4-吡啶的组合可以在各种醇，酯和醚溶剂中偶联，达到50克的规模。在4-二甲氨基-2-氯吡啶还原均偶联的基础上，改进合成了最佳配体4,4′-双（二甲氨基）-2,2′-联吡啶。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.