Vinyl Sulfonium Salts as the Radical Acceptor for Metal-Free Decarboxylative Alkenylation

Vinyl sulfonium salts typically act as an electrophilic Michael acceptor, thus initiating many tandem cyclization reactions. Herein, we disclosed the novel reactivity of vinyl sulfonium salts as a radical acceptor. Using redox-active ester as an alkyl radical precursor, metal-free decarboxylative al...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2020-10, Vol.22 (19), p.7768-7772
Main Authors: Zhang, Yu-Lan, Yang, Lei, Wu, Jie, Zhu, Chunyin, Wang, Peng
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:Vinyl sulfonium salts typically act as an electrophilic Michael acceptor, thus initiating many tandem cyclization reactions. Herein, we disclosed the novel reactivity of vinyl sulfonium salts as a radical acceptor. Using redox-active ester as an alkyl radical precursor, metal-free decarboxylative alkenylation with vinyl sulfonium salts was realized using eosin Y as a photocatalyst. This process features a broad substrate scope and tolerates with a broad range of primary, secondary, tertiary carboxylic acids.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03074