Pull–Pull Halogenated β‐Cyanoacrylates in Aza‐Michael Reaction: Intriguing Problem of Regioselectivity

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI:10.1002/ajoc.202500414

Ilya A. Tyumentsev , Igor A. Ushakov , Anton V. Kuzmin , Alexander Yu. Rulev

引用次数: 0

Abstract

The controlled regioselective addition of nitrogen‐centered nucleophiles to the pull–pull halogenated β‐cyanoacrylates is a challenging problem in the chemistry of pull–pull alkenes due to the close electronic properties of the vicinal acceptor groups. The influence of the type of halogen and its position on the double bond, as well as the amine nucleophilicity and the presence of additives on the direction of addition have been studied. The experimental data are in excellent agreement with the density functional theory (DFT) calculations.

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Aza-Michael反应中拉-拉卤化β-氰基丙烯酸酯：区域选择性的有趣问题

氮中心亲核试剂在拉-拉卤化β-氰基丙烯酸酯上的可控区域选择性加成是拉-拉烯烃化学中的一个具有挑战性的问题，因为相邻受体基团的电子性质非常接近。研究了卤素的种类和位置对双键的影响，以及胺的亲核性和助剂的存在对加成方向的影响。实验数据与密度泛函理论（DFT）计算结果非常吻合。

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

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.