Elucidation of a Parasitic Proton-Coupled Electron Transfer in a Photocatalytic Benzylic C-H Sulfonamidation.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-13 Epub Date: 2025-06-03 DOI:10.1021/acs.orglett.5c01637

Nicholas A Fitzpatrick, Anna M Howarth, Grzegorz J Skrzypek, Jisun Lee, Hatice G Yayla, Patricia Z Musacchio

引用次数: 0

Abstract

Strategies for C-H amination with sulfonamides have been dominated by stoichiometric strategies or Rh/Cu catalysis using strong oxidants, elevated temperatures, or excess equivalents of C-H partner. We developed a photocatalytic C-H amination with a bench-stable N-methoxypyridinium salt that is amenable to late-stage functionalization efforts. We discovered a competitive proton-coupled electron transfer pathway between sulfonamide and a pyridine byproduct that inhibits the reaction. Catalysis was re-established with the introduction of ZnBr₂.

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光催化苄基C-H磺化反应中寄生质子耦合电子转移的研究。

磺胺类C-H胺化的策略主要是化学计量策略或使用强氧化剂、高温或过量等价物的Rh/Cu催化。我们用稳定的n -甲氧基吡啶盐开发了一种光催化的C-H胺化反应，该反应可用于后期功能化。我们发现了磺胺和吡啶副产物之间的竞争性质子耦合电子转移途径，抑制了反应。引入ZnBr2后，重新建立了催化反应。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.