Fast Heating‐Assisted One‐Pot Copper‐Catalyzed Sulfonylation and Sulfochlorination of Styrenes

Here, a strategy for the synthesis under fast‐heating conditions of vinyl sulfones and β‐chlorosulfones from styrene derivatives, tosyl chloride (TsCl) as sulfonyl and chlorine source, and CuBr‐neocuproine as the catalytic system is reported. The reaction occurs through an atom transfer radical addi...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2022-08, Vol.2022 (29), p.n/a
Main Authors: Saavedra‐Olavarría, Jorge, Hermosilla‐Ibáñez, Patricio, Almodóvar, Iriux, Pérez, Edwin G.
Format: Article
Language:English
Subjects:
Adducts
Catalysis
Chlorine
Copper
Heating
One pot synthesis
Reagents
Styrenes
Sulfochlorination
Sulfones
Sulfonylation
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:Here, a strategy for the synthesis under fast‐heating conditions of vinyl sulfones and β‐chlorosulfones from styrene derivatives, tosyl chloride (TsCl) as sulfonyl and chlorine source, and CuBr‐neocuproine as the catalytic system is reported. The reaction occurs through an atom transfer radical addition (ATRA) mechanism to generate the sulfochlorinated adducts followed by E2 elimination to generate the vinyl sulfones. This methodology allows a wide range of vinyl sulfones and β‐chlorosulfones to be obtained using inexpensive reagents in one and five minutes respectively. These reactions appear as an interesting fast and easy‐to‐handle alternative to obtain these compounds. We report a one‐pot copper‐catalyzed sulfonylation and sulfochlorination of styrenes under fast heating conditions. Optimization, substrate scope, and detailed procedures are discussed. The reactions showed moderate to excellent yields and appear as an interesting fast and easy‐to‐handle alternative to obtain β‐chloro‐ or vinylsulfones.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101526