Tertiary Alkyl Hantzsch Nitriles as a Redox-Neutral Platform for All-Carbon Quaternary Centers Construction via Bimolecular Homolytic Substitution (SH2)

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-15 DOI:10.1021/acs.orglett.6c04412

Yuxuan Wan,Yu Chen,Caiyun He,Tao Yang

引用次数: 0

Abstract

Abstract The construction of quaternary carbon centers remains an important yet challenging goal in synthetic chemistry. Herein, we report a photochemical nickel-mediated coupling of tertiary 4-alkyl Hantzsch nitriles derived from alkyl aldehydes with redox-active esters of primary carboxylic acids to forge sterically congested C(sp3)–C(sp3) bonds via SH2 under redox-neutral conditions. Two reaction protocols were established: one operates under 390 nm irradiation, whereas the other employs blue-light irradiation in the presence of an exogenous photocatalyst. These operationally simple protocols exhibit excellent functional group tolerance and provide general access to all-carbon quaternary centers from a previously unexplored substrate combination.

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叔烷基汉氏腈作为双分子均解取代（SH2）构建全碳季中心的氧化还原中性平台

在合成化学中，构建季碳中心一直是一个重要而又具有挑战性的课题。在此，我们报道了由烷基醛衍生的叔4-烷基Hantzsch腈与伯羧酸的氧化还原活性酯在氧化还原中性条件下通过SH2形成立体密集的C(sp3) -C （sp3）键的光化学镍介导偶联。建立了两种反应方案：一种在390 nm照射下操作，而另一种在外源光催化剂的存在下使用蓝光照射。这些操作简单的方案表现出优异的官能团耐受性，并提供了从以前未开发的底物组合中获得全碳季中心的一般途径。

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.