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远程氟化和氟烷基(硫)化反应。

Remote Fluorination and Fluoroalkyl(thiol)ation Reactions.

机构信息

Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Frontiers Science Center for Synthetic Biology (Ministry of Education), and Tianjin Collaborative Innovation Center of Chemical Science & Engineering, Tianjin University, Tianjin, 300072, China.

Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa, 3200009, Israel.

出版信息

Chemistry. 2020 Dec 1;26(67):15378-15396. doi: 10.1002/chem.202003416. Epub 2020 Oct 22.

DOI:10.1002/chem.202003416
PMID:32779797
Abstract

Remote functionalization reactions have the power to transform a C-H (or C-C) bond at a distant position from a functional group. This Review summarizes recent advances and key breakthroughs in remote fluorination, trifluoromethylation, difluoromethylation, trifluoromethylthiolation, and fluoroalkenylation reactions. Several powerful strategies have emerged to control the reactivity and distal selectivity such as the undirected radical approach, the 1,5-hydrogen atom transfer, the metal migration, the use of distant directing groups, and the ring-opening reactions. These unconventional and predictable C-H (and C-C) functionalization transformations should allow for the preparation of a wide range of otherwise-difficult-to-access alkyl, aromatic, heteroaromatic, and structurally complex fluorides.

摘要

远程官能团化反应具有在远离官能团的位置将 C-H(或 C-C)键转化为功能基团的能力。本综述总结了远程氟化、三氟甲基化、二氟甲基化、三氟甲硫基化和氟烯基化反应的最新进展和关键突破。已经出现了几种强大的策略来控制反应性和远程选择性,例如无导向自由基方法、1,5-氢原子转移、金属迁移、使用远程导向基团和开环反应。这些非常规和可预测的 C-H(和 C-C)官能团化转化应该能够制备广泛的其他难以获得的烷基、芳基、杂芳基和结构复杂的氟化物。

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