Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Angewandte Chemie, vol. 136

Abstract

Abstract Benzo[1,3,2]dithiazole‐1,1,3‐trioxides are bench‐stable and easy‐to‐use reagents. In photoredox catalysis, they generate methyl and perdeuteromethyl radicals which can add to a variety of radical acceptors, including olefins, acrylamides, quinoxalinones, isocyanides, enol silanes, and N ‐Ts acrylamide. As byproduct, a salt is formed which can be regenerated to the original methylating agent. Flow chemistry provides an option for reaction scale‐up further underscoring the synthetic usefulness of these methylation reagents. Mechanistic investigations suggest a single‐electron transfer (SET) pathway induced by photoredox catalysis.

Authors 9

1. Peng Wu Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 52074 Aachen Germany

   RWTH Aachen University Chemistry GERMANY

2. Gabriel Goujon

   Université Paris-Saclay · Institut Lavoisier de Versailles

   Affiliation as printed

   Institut Lavoisier de Versailles Université Paris-Saclay 78000 Versailles France

   Universite Paris-Saclay Chemistry FRANCE

3. Shulei Pan Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 52074 Aachen Germany

   RWTH Aachen University Chemistry GERMANY

4. Béatrice Tuccio

   Centre National de la Recherche Scientifique · Aix-Marseille Université · Institut de Chimie Radicalaire

   Affiliation as printed

   Aix-Marseille Université CNRS, Institut de Chimie Radicalaire, UMR 7273 F-13397 Marseille Cedex 20 France

   Aix-Marseille Universite Chemistry FRANCE

5. Bruce Pégot

   Université Paris-Saclay · Institut Lavoisier de Versailles

   Affiliation as printed

   Institut Lavoisier de Versailles Université Paris-Saclay 78000 Versailles France

   Universite Paris-Saclay Chemistry FRANCE

6. Guillaume Dagousset

   Université Paris-Saclay · Institut Lavoisier de Versailles

   Affiliation as printed

   Institut Lavoisier de Versailles Université Paris-Saclay 78000 Versailles France

   Universite Paris-Saclay Chemistry FRANCE

7. Elsa Anselmi

   Université Paris-Saclay · Université de Tours · Institut Lavoisier de Versailles

   Affiliation as printed

   Institut Lavoisier de Versailles Université Paris-Saclay 78000 Versailles France

   Université de Tours Faculté des Sciences et Techniques 37200 Tours France

   Universite Paris-Saclay Chemistry FRANCE

8. Emmanuel Magnier

   Université Paris-Saclay · Institut Lavoisier de Versailles

   Affiliation as printed

   Institut Lavoisier de Versailles Université Paris-Saclay 78000 Versailles France

   Universite Paris-Saclay Chemistry FRANCE

9. Carsten Bolm Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 52074 Aachen Germany

   RWTH Aachen University: Rheinisch-Westfalische Technische Hochschule Aachen Chemistry Landoltweg 1 52056 Aachen GERMANY