可见光诱导C(sp3) -H键与三甲基硅酰氯作为双功能试剂的二氟烷基化

IF 4.4 2区 化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2025-01-09 DOI:10.1002/adsc.202401497
Xiaochen Wang, Senhui Wu, Pengxuan Ding, Yuxiu Liu, Hong-Jian Song, Qing-Min Wang
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引用次数: 0

摘要

本文报道了一种温和、操作简单的合成α,α -二氟酮的方法,通过三氟酮的选择性单次脱氟和C(sp3) -H键的二氟烷基化,在室温下一步合成α,α -二氟酮。通过成功地将非官能化醚和苯基前体二氟烷基化,我们证明了该方法的广泛适用性。机理研究表明,该反应的成功可能归因于三甲基硅氯在光催化条件下的双重作用:1)氟离子阴离子清除剂;2)促进氢原子转移(HAT)反应的氯自由基源。
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Visible‐light‐induced Difluoroalkylation of C(sp3)–H Bonds with Trimethylsilyl Chloride as a Dual‐function Reagent
Herein, we report a mild, operationally simple method for synthesis of α,α‐difluoroketones through selective single defluorination of trifluoroketones and subsequent difluoroalkylation of C(sp3)–H bonds at room temperature within a single step. By successfully difluoroalkylating unfunctionalized ethers and benzyl radical precursors, we demonstrated the broad applicability of this method. The mechanistic study supports that the success of the reaction is probably attributed to the dual roles of trimethylsilyl chloride under the photocatalyzed conditions: 1) fluoride anion scavenger; and 2) chlorine radical source which promote hydrogen atom transfer (HAT) reaction.
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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