Generation of Sulfamoyl Radicals via Visible-Light Mediated Fixation of Sulfur Dioxide for the Synthesis of Sulfonamides

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-10-18 DOI:10.1002/adsc.202401065

Thaís Rodrigues Arroio, Jan Philipp Nau, Kamil Hofman, Christoph Förster, Stephanie L. Faber, Sabine Becker, Katja Heinze, Giuliano Cesar Clososki, Georg Manolikakes

引用次数: 0

Abstract

Abstract. Herein, we report a new approach for the light-mediated generation of sulfamoyl radicals using sulfur dioxide as key building block and the direct application of these radicals in the synthesis of sulfonamides. In the presence of different photoredox catalysts, sulfamoyl radicals can be generated directly from SO2 or the SO2 surrogate DABSO (1,4-diazabicyclo[2.2.2]octane·bis (sulfur dioxide) adduct) and N-aminopyridinium salts as nitrogen radical precursors. Trapping of the in situ generated sulfamoyl radicals with selected electron-rich olefins affords different sulfonamides in up to 86% yield in a three-component procedure. This transformation provides an attractive and complementary approach for the in situ generation of sulfamoyl radicals as synthetic intermediates for the assembly of the sulfonamide functionality, a motif in active pharmaceutical ingredients.

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通过可见光介导的二氧化硫固定作用生成磺酰胺基自由基以合成磺酰胺类化合物

摘要在此，我们报告了一种以二氧化硫为关键构筑基块，通过光介导生成氨基磺酰基的新方法，以及这些自由基在磺胺类药物合成中的直接应用。在不同的光氧化催化剂存在下，可直接从二氧化硫或二氧化硫代用品 DABSO（1,4-二氮杂双环[2.2.2]辛烷-双（二氧化硫）加合物）和 N-氨基吡啶鎓盐作为氮自由基前体生成氨基磺酰基。用选定的富电子烯烃捕获原位生成的氨基磺酰基，在三组份过程中生成不同的磺酰胺，收率高达 86%。这种转化为原位生成氨基磺酰基提供了一种极具吸引力的互补方法，可作为组装磺酰胺官能团（活性药物成分中的一种主题）的合成中间体。

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

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.