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用于双氟烯烃官能化的氟保留策略。

Fluorine-Retentive Strategies for the Functionalization of -Difluoroalkenes.

作者信息

Sorrentino Jacob P, Altman Ryan A

机构信息

Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66045, United States.

Department of Medicinal Chemistry and Molecular Pharmacology and Department of Chemistry, Purdue University, West Lafayette, Indiana 47906, United States.

出版信息

Synthesis (Stuttg). 2021 Nov;53(21):3935-3950. doi: 10.1055/a-1547-9270.

Abstract

-Difluoroalkenes are readily available fluorinated building blocks, and the fluorine-induced electronic perturbations of the alkenes enables a wide array of selective functionalization reactions. However, many reactions of -difluoroalkenes result in a net C─F functionalization to generate monofluorovinyl products or addition of F to generate trifluoromethyl-containing products. In contrast, fluorine-retentive strategies for the functionalization of -difluoroalkenes remain less generally developed, and is now becoming a rapidly developing area. This review will present the development of fluorine-retentive strategies including electrophilic, nucleophilic, radical, and transition metal catalytic strategies with an emphasis on key physical organic and mechanistic aspects that enable reactivities.

摘要

二氟烯烃是易于获得的氟化结构单元,烯烃中氟诱导的电子扰动使得一系列选择性官能团化反应成为可能。然而,许多二氟烯烃的反应会导致净的C─F官能团化,生成单氟乙烯基产物,或者添加氟生成含三氟甲基的产物。相比之下,二氟烯烃官能团化的氟保留策略总体上仍未得到充分发展,而现在正成为一个快速发展的领域。本综述将介绍氟保留策略的发展,包括亲电、亲核、自由基和过渡金属催化策略,重点关注能够实现反应活性的关键物理有机和机理方面。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c10c/8545266/78555bf8fee9/nihms-1723662-f0004.jpg

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