Solvent Controlled Palladium-Catalyzed β-Regioselective Hydroamination of Allenoates with Azole Heterocycles

IF 4.5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2026-09-23 DOI:10.1039/d6qo01177b

Kaixuan Pan,Xin Bai,Wanshu Wang,Lu Gao,Zhenlei Song,Xiaoxiao Tang

引用次数: 0

Abstract

Herein, we report a solvent-controlled palladium-catalyzed regiodivergent hydroamination of allenoates with azole heterocycles. By simply switching solvent polarity and coordination ability, two structurally distinct β-regioselective products-a kinetic non-conjugated isomer and a thermodynamic conjugated isomer-are exclusively formed under mild conditions. Mechanistic studies reveal that solvent modulates the coordination environment of the π-allyl Pd(II) intermediate, enabling switchable σ-π-σ isomerization and site-selective protonation. This operationally simple approach provides efficient access to diverse β-azole-substituted alkenes with precise control over selectivity.

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溶剂控制钯催化的含唑杂环烯丙酸酯的β-区域选择性胺化反应

本文报道了一种溶剂控制的钯催化的含唑杂环烯丙酸盐的区域发散性氢胺化反应。通过简单地改变溶剂极性和配位能力，两种结构不同的β-区域选择性产物——动力学非共轭异构体和热力学共轭异构体——在温和的条件下完全形成。机理研究表明，溶剂调节了π-烯丙基Pd（II）中间体的配位环境，实现了可切换的σ-π-σ异构化和位点选择性质子化。这种操作简单的方法提供了有效的访问不同的β-唑取代烯烃与精确控制的选择性。

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 Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.