Carboxylate-Directed Oxidative Annulation via C(Alkenyl)－H Activation/Double Alkyne Insertion/1,4-Pd Migration: Synthesis of Functionalized Naphthalenes

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-10-31 DOI:10.1002/adsc.202400973

Chih-Ming Chou, Cheng-Hao Fu, Manjaly J. Ajitha, Veerabhushanam Kadiyala, Yu-Chun Wang, Tzu-Yu Hsu, I-Hsuan Sung, Kuo-wei Huang

引用次数: 0

Abstract

A palladium-catalyzed double consecutive C(alkenyl)–H activation/alkyne insertion method utilizing a free carboxylic acid as a directing group in the preparation of functionalized naphthalenes is reported. The reaction mechanism involves a sequence of the C (alkenyl)−H activation/alkyne insertion/1,4-palladium migration/reductive elimination steps. The second alkyne insertion occurred at the phenyl ring of the intermediate generated from the first alkyne insertion via 1,4-palladium migration, which is an uncommon case in typical C–H activation/alkyne insertion chemistry, providing functionalized naphthalene products. Additionally, the kinetic studies and control experiments as well as density functional theory (DFT) studies are also investigated to elucidate the reaction mechanism.

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通过 C(烯基)-H 活化/双炔插入/1,4-钯迁移的羧酸盐导向氧化环化：功能化萘的合成

报告了一种利用游离羧酸作为指导基团的钯催化双连续 C（烯基）-H 活化/炔插入法制备官能化萘。反应机理包括一连串的 C（烯基）-H 活化/炔插入/1,4-钯迁移/还原消除步骤。第二个炔插入发生在第一个炔插入通过 1,4 钯迁移生成的中间体的苯基环上，这在典型的 C-H 活化/炔插入化学中并不常见，从而提供了官能化的萘产物。此外，还进行了动力学研究和对照实验以及密度泛函理论（DFT）研究，以阐明反应机理。

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.