Photocatalytic Radical Cascade Dehalogenation/Carbo-cyclization/Sulfonylation Leading to Indole- and Benzofuran-Based Benzylic Sulfones

This study presents a convenient approach to the synthesis of indole- and benzofuran-based benzylic sulfones using unactivated alkynes containing aryl iodides and sodium sulfinates under visible light irradiation. The procedure involves a sequential series of dehalogenation, carbo-cyclization, and r...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2023-12, Vol.88 (24), p.17227-17236
Main Authors: Liu, Qing-Quan, Li, Jia-Zhuo, Wang, Yan-Jing, Leng, Yan-Ning, Huang, Yu-Wen, Meng, Xin-Chao, Leng, Bo-Rong, Wang, De-Cai, Zhu, Yi-Long
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:This study presents a convenient approach to the synthesis of indole- and benzofuran-based benzylic sulfones using unactivated alkynes containing aryl iodides and sodium sulfinates under visible light irradiation. The procedure involves a sequential series of dehalogenation, carbo-cyclization, and radical sulfonylation. Plausible insights into the reaction mechanism are derived from control experiments, leading to the proposal of a radical cascade reaction pathway.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02068