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光化学 Sonogashira 偶联反应:超越传统钯 - 铜催化

Photochemical Sonogashira coupling reactions: beyond traditional palladium-copper catalysis.

作者信息

Singh Puja, Shaikh Aslam C

机构信息

Department of Chemistry, Indian Institute of Technology, Ropar (IIT Ropar), Rupnagar, Punjab-140 001, India.

出版信息

Chem Commun (Camb). 2023 Sep 28;59(78):11615-11630. doi: 10.1039/d3cc03855f.

DOI:10.1039/d3cc03855f
PMID:37697801
Abstract

Sonogashira coupling is one of the Nobel reactions discovered in 1975 to form a C-C bond using palladium and copper as co-catalysts. Incorporating alkyne functionalities either in macro or micro molecules by using this Sonogashira reaction has already proven its viability and relevance in the sphere of synthetic chemistry. While aiming for sustainable chemistry, in recent years, visible light photoredox catalysts have appeared as an advanced tool in this regard. In this review, we aim to portray a comprehensive summary of modern visible light photo redox catalyzed Sonogashira reaction, which will leave space for the readers to rethink alternative strategies to conduct the Sonogashira reaction. This review briefly describes the implementation of various metal-based nanomaterial photocatalysts, developing either copper or palladium-free photocatalytic methods, and organo-photolytic and bioinspired photocatalysts for the Sonogashira coupling reactions. Besides, this review also gives a concise overview of the mechanistic aspects and highlights selective examples for substrate scope.

摘要

Sonogashira偶联反应是1975年发现的诺奖反应之一,该反应使用钯和铜作为共催化剂形成碳-碳键。通过Sonogashira反应在大分子或小分子中引入炔基官能团,已在合成化学领域证明了其可行性和实用性。近年来,在追求可持续化学的过程中,可见光光氧化还原催化剂已成为这方面的一种先进工具。在本综述中,我们旨在全面总结现代可见光光氧化还原催化的Sonogashira反应,这将为读者重新思考进行Sonogashira反应的替代策略留出空间。本综述简要描述了各种基于金属的纳米材料光催化剂的应用,开发不含铜或钯的光催化方法,以及用于Sonogashira偶联反应的有机光解和仿生光催化剂。此外,本综述还简要概述了反应机理方面,并突出了底物范围的选择性实例。

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