Visible-Light-Induced Radical Cascade Sulfonylation/Cyclization to Access Sulfonylated Benzazepines and Benzoxepines by EDA Complexes
Abstract
A visible light-mediated sulfonylation of 1-(2-(allyloxy)aryl)-3,3-bis(methylthio)prop-2-en-1-ones and N -allyl- N -(2-(3,3-bis(methylthio) acryloyl)aryl)-4-methylbenzenesulfonamides for the synthesis of a wide range of sulfonylated benzazepines and benzoxepines is developed. This protocol features simple operation, photocatalyst- and additive-free, good regioselectivity, and the use of K 2 S 2 O 5 as a sulfur dioxide substitute, providing a novel environmentally friendly strategy to access the seven-membered heterocycles. The mechanistic studies revealed that aryldiazonium tetrafluoroborates served as electron acceptors, enabling the formation of EDA complexes with α-oxoketene dithioacetal substrates.
Fields of Study & Subjects
Sulfur-Based Synthesis Techniques
Radical Photochemical Reactions
Click Chemistry and Applications
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 22
- Pages
- 7537–7547
- Publication date
- 23 May 2026
- Language
- EN