Relay C(sp3)-H bond trifluoromethylthiolation and amidation by visible light photoredox catalysis

IF 10.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Science China Chemistry Pub Date : 2024-10-12 DOI:10.1007/s11426-024-2259-7
Junheng Liu, Suqi Yang, Shunruo Yao, Chengjian Zhu, Yong Liu, Weipeng Li, Jin Xie
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Abstract

Selective functionaliz0ation of C(sp3)–H bonds is a straightforward and practical method to construct complex molecule skeletons. In this field, direct transformation of unactivated C(sp3)–H bonds into C(sp3)–SCF3 architectures is still a great challenge. We report a highly selective trifluoromethylthiolation of unactivated aliphatic C(sp3)–H bonds by combination of proton-coupled electron transfer (PCET) and hydrogen atom transfer (HAT) strategy. A wide range of structurally diverse alkyl trifluoromethyl sulfides are obtained. Furthermore, the use of two different photocatalysts can realize an unprecedented trifluoromethylthiolation and amidation cascade of different C(sp3)–H bonds. It can afford a good access to bifunctionalized molecules in synthetically useful yields.

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利用可见光光氧化催化中继 C(sp3)-H键三氟甲基硫代和酰胺化反应
C(sp3)-H 键的选择性官能化是构建复杂分子骨架的一种直接而实用的方法。在这一领域,将未活化的 C(sp3)-H 键直接转化为 C(sp3)-SCF3 结构仍然是一个巨大的挑战。我们报告了通过结合质子耦合电子转移(PCET)和氢原子转移(HAT)策略,对未活化的脂肪族 C(sp3)-H 键进行高选择性三氟甲基硫代反应的情况。结果获得了多种结构不同的三氟甲基烷基硫化物。此外,使用两种不同的光催化剂可以实现前所未有的不同 C(sp3)-H 键的三氟甲基硫代和酰胺化级联反应。这为合成双官能团分子提供了良好的途径。
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来源期刊
Science China Chemistry
Science China Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
14.40
自引率
7.30%
发文量
3787
审稿时长
2.2 months
期刊介绍: Science China Chemistry, co-sponsored by the Chinese Academy of Sciences and the National Natural Science Foundation of China and published by Science China Press, publishes high-quality original research in both basic and applied chemistry. Indexed by Science Citation Index, it is a premier academic journal in the field. Categories of articles include: Highlights. Brief summaries and scholarly comments on recent research achievements in any field of chemistry. Perspectives. Concise reports on thelatest chemistry trends of interest to scientists worldwide, including discussions of research breakthroughs and interpretations of important science and funding policies. Reviews. In-depth summaries of representative results and achievements of the past 5–10 years in selected topics based on or closely related to the research expertise of the authors, providing a thorough assessment of the significance, current status, and future research directions of the field.
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