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利用（苯磺酰基）二氟甲基锍盐：一种通过光氧化还原催化实现不饱和化合物与PhSOCF基团官能化的自由基方法。

Harnessing (Phenylsulfonyl)difluoromethyl Sulfonium Salt: A Radical Approach to Photoredox-Catalyzed Functionalization of Unsaturated Compounds with the PhSOCF Group.

作者信息

Roy Sourav, Besset Tatiana

机构信息

INSA Rouen Normandie, Univ. Rouen Normandie, CNRS, Normandie Univ., Institut CARMeN, UMR 6064, Rouen F-76000, France.

出版信息

JACS Au. 2025 May 22;5(6):2556-2566. doi: 10.1021/jacsau.5c00169. eCollection 2025 Jun 23.

DOI:10.1021/jacsau.5c00169
PMID:40575319
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12188395/
Abstract

A photoredox-catalyzed, modular method for the synthesis of versatile (phenylsulfonyl)-difluoromethylated compounds is presented. The key step in this transformation is the light-driven generation of a fluoroalkyl radical from our in-house-designed (phenylsulfonyl)-difluoromethyl sulfonium salt. Tuning the reactivity of this fluorinated sulfonium salt under photocatalysis provided an efficient tool for the direct functionalization of readily available olefins. Notably, the photocatalyzed difunctionalization of alkenes, as well as three- or four-component reactions, were studied, providing efficient access to an array of difluoroalkylated linear or cyclic products. Mechanistic studies have been conducted to provide a better understanding of the reaction mechanism for the synthesis of (phenylsulfonyl)-difluoromethylated alkenes. Exploring the reactivity of the (phenylsulfonyl)-difluoromethyl salt under photocatalysis has led to a straightforward, versatile strategyakin to a "Swiss army knife"for accessing a wide range of (phenylsulfonyl)-difluoromethyl-containing molecules.

摘要

本文介绍了一种光氧化还原催化的模块化方法，用于合成通用的（苯磺酰基）-二氟甲基化化合物。该转化的关键步骤是由我们自行设计的（苯磺酰基）-二氟甲基锍盐通过光驱动生成氟烷基自由基。在光催化作用下调节这种氟化锍盐的反应活性，为现成烯烃的直接官能团化提供了一种有效工具。值得注意的是，研究了光催化的烯烃双官能团化以及三组分或四组分反应，从而能够高效地获得一系列二氟烷基化的线性或环状产物。已进行机理研究，以更好地理解（苯磺酰基）-二氟甲基化烯烃合成的反应机理。探索（苯磺酰基）-二氟甲基盐在光催化下的反应活性，已产生了一种直接、通用的策略——类似于“瑞士军刀”——用于获取多种含（苯磺酰基）-二氟甲基的分子。

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