Recent Advances in Alkenyl sp2 C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

IF 51.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Ming-Zhu Lu, Jeffrey Goh, Manikantha Maraswami, Zhenhua Jia, Jie-Sheng Tian and Teck-Peng Loh*, 
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引用次数: 25

Abstract

Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, and advanced materials. Significant efforts have been made toward the development of new and practical methods to access this important class of compounds by selectively activating the alkenyl C(sp2)–H bonds in recent years. In this comprehensive review, we describe the state-of-the-art strategies for the direct functionalization of alkenyl sp2 C–H and C–F bonds until June 2022. Moreover, metal-free, photoredox, and electrochemical strategies are also covered. For clarity, this review has been divided into two parts; the first part focuses on currently available alkenyl sp2 C–H functionalization methods using different alkene derivatives as the starting materials, and the second part describes the alkenyl sp2 C–F bond functionalization using easily accessible gem-difluoroalkenes as the starting material. This review includes the scope, limitations, mechanistic studies, stereoselective control (using directing groups as well as metal-migration strategies), and their applications to complex molecule synthesis where appropriate. Overall, this comprehensive review aims to document the considerable advancements, current status, and emerging work by critically summarizing the contributions of researchers working in this fascinating area and is expected to stimulate novel, innovative, and broadly applicable strategies for alkenyl sp2 C–H and C–F bond functionalizations in the coming years.

Abstract Image

烯基sp2 C-H和C-F键功能化的研究进展:范围、机理和应用
烯烃及其衍生物广泛应用于各种天然产品、药品和先进材料中。近年来,通过选择性激活烯基C(sp2) -H键来获得这类重要化合物的新方法已经取得了重大进展。在这篇综合综述中,我们描述了到2022年6月为止烯基sp2 C-H和C-F键直接功能化的最新策略。此外,无金属、光氧化还原和电化学策略也被涵盖。为清楚起见,本文分为两部分;第一部分重点介绍了目前可用的以不同烯烃衍生物为起始材料的烯基sp2 C-H功能化方法,第二部分描述了以易获取的宝石二氟烯烃为起始材料的烯基sp2 C-F键功能化方法。本文综述了其范围、局限性、机理研究、立体选择控制(使用定向基团和金属迁移策略)及其在复杂分子合成中的应用。总的来说,这篇全面的综述旨在通过批判性地总结研究人员在这一迷人领域的贡献来记录相当大的进展、现状和新兴的工作,并期望在未来几年激发新的、创新的、广泛适用的烯基sp2 C-H和C-F键功能化策略。
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
Chemical Reviews
Chemical Reviews 化学-化学综合
CiteScore
106.00
自引率
1.10%
发文量
278
审稿时长
4.3 months
期刊介绍: Chemical Reviews is a highly regarded and highest-ranked journal covering the general topic of chemistry. Its mission is to provide comprehensive, authoritative, critical, and readable reviews of important recent research in organic, inorganic, physical, analytical, theoretical, and biological chemistry. Since 1985, Chemical Reviews has also published periodic thematic issues that focus on a single theme or direction of emerging research.
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