Synthesis of α-Cyano-β-naphthylamines via Tandem Selective Hydrocyanation of Unactivated Alkynes and Thorpe Reaction

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-14 DOI:10.1021/acs.orglett.6c04271

Weiming Chen,Teng Liu,Tao Zhu,Lechi Zhang,Qilinjing Li,Yiwen Wang,Zishuo Li,Rongxin Su,Junyuan Hu,Jiuzhong Huang

引用次数: 0

Abstract

Abstract An unprecedented nickel-catalyzed tandem reaction involving alkyne hydrocyanation and sequential Thorpe reaction has been developed. By employing readily available and less toxic Zn(CN)2 as the cyanide source, both selective alkyne hydrocyanation and tandem cyclization are achieved in a substrate-controlled manner. Mechanistic studies and DFT calculations confirm that the alkenyl nitrile serves as a key intermediate, and hydrogen transfer is identified as the rate-determining step in the Thorpe reaction. This work offers a novel strategy for the construction of α-cyano-β-naphthylamine via a cascade reaction mode.

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非活化炔烃串联选择性氢化反应合成α-氰基-β-萘胺

摘要建立了一种前所未有的镍催化烷基氢氰化和顺序索普反应的串联反应。采用易得且毒性较低的Zn(CN)2作为氰化物源，在底物控制下实现了选择性炔氢化反应和串联环化反应。机理研究和DFT计算证实，烯基腈是一个关键的中间体，氢转移被确定为索普反应的速率决定步骤。这项工作为通过级联反应模式构建α-氰基-β-萘胺提供了一种新的策略。

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.