Regioselective Organocatalyzed Monochlorination of Arenes with Electrophilic Chlorosulfoniums

Author:

Garay‐Talero Alexander1,Acosta‐Guzmán Paola12,Gamba‐Sánchez Diego1ORCID

Affiliation:

1. Laboratory of Organic Synthesis, Bio and Organocatalysis Chemistry Department Universidad de Los Andes Cra. 1 No. 18A-12 Q:305. 111711 Bogotá Colombia

2. Current Adress: Departamento de Química Facultad de Ciencias Universidad Nacional de Colombia 111321 Bogotá Colombia

Abstract

AbstractThis manuscript presents a regioselective chlorination of arenes, yielding almost exclusively the monochlorinated product. It tolerates free hydroxy groups, 1°, 2° and 3° amines, and carboxylic acids, among other polar and nonpolar functional groups, as well as mono‐ and polysubstituted aromatic rings. Additionally, the utilization of chlorosulfonium salts as the chlorinating agent is demonstrated. The method emerges as an alternative to other processes where organic byproducts must be separated from the reaction mixture. In addition, the main byproducts are gaseous materials such as CO and CO2. This publication introduces the application of sulfoxides, oxalyl chloride, and aqueous hydrogen peroxide as the chlorination mixture.

Publisher

Wiley

Subject

General Chemistry

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