A Visible-Light-Induced α-H Chlorination of Alkylarenes with Inorganic Chloride under NanoAg@AgCl

Shouxin Liu; Qi Zhang; Huiying Li; Yihua Yang; Xia Tian; Andrew Whiting

doi:10.1002/chem.201501439

A Visible-Light-Induced α-H Chlorination of Alkylarenes with Inorganic Chloride under NanoAg@AgCl

Chemistry. 2015 Jun 26;21(27):9671-5. doi: 10.1002/chem.201501439. Epub 2015 Jun 8.

Authors

Shouxin Liu¹, Qi Zhang², Huiying Li², Yihua Yang², Xia Tian², Andrew Whiting³

Affiliations

¹ State Key Laboratory Breeding Base, Hebei Province, Key Laboratory of Molecular Chemistry for Drugs, Hebei University of Science & Technology, Shijiazhuang 050018 (P. R. China), Fax: (+86) 311-88632002. chlsx@hebust.edu.cn.
² State Key Laboratory Breeding Base, Hebei Province, Key Laboratory of Molecular Chemistry for Drugs, Hebei University of Science & Technology, Shijiazhuang 050018 (P. R. China), Fax: (+86) 311-88632002.
³ Centre for Sustainable Chemical Processes, Department of Chemistry, Science Laboratories, Durham University, South Road Durham, DH1 3LE (UK), Fax: (+44) 191-384-4737. andy.whiting@durham.ac.uk.

PMID: 26061749
DOI: 10.1002/chem.201501439

Abstract

An efficient, photocatalytic chlorination of alkylarene α-H groups using NaCl/HCl as a chlorine source has been developed, which involves a radical mechanism under visible-light (including sunlight) conditions. A chlorine radical is proposed to be formed by an electron transfer from chloride ion to O2 in air through the bandgap hole of the semiconductor AgCl. The chlorination protocol is characterized by its use of natural sunlight or other visible light, mild conditions, cheap source of chlorine, green solvent, and high selectivity. The yield of benzylchloride is 95% with a toluene conversion as high as 40%, which rivals traditional chlorination methods.

Keywords: NaCl/HCl; alkylarenes; chlorination; nano-Ag; photocatalyst.

Publication types

Research Support, Non-U.S. Gov't