Reductive Homocoupling of Organohalides Using Nickel(II) Chloride and Samarium Metal

Yongjun Liu; Shuhuan Xiao; Yan Qi; Feng Du

doi:10.1002/asia.201601712

Reductive Homocoupling of Organohalides Using Nickel(II) Chloride and Samarium Metal

Chem Asian J. 2017 Mar 16;12(6):673-678. doi: 10.1002/asia.201601712. Epub 2017 Feb 21.

Authors

Yongjun Liu¹, Shuhuan Xiao¹, Yan Qi¹, Feng Du¹

Affiliation

¹ State Key Laboratory Base of Eco-chemical Engineering, Key Laboratory of Sensor Analysis of Tumor Marker, Ministry of Education, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, P. R. China.

PMID: 28124471
DOI: 10.1002/asia.201601712

Abstract

A homocoupling method for organohalides and organosulfonates promoted by samarium metal and HMPA, and catalyzed by NiCl₂ has been developed. Various organohalides (benzyl, aryl, heterocyclic, alkenyl and alkyl halides), α-haloacetophenones, and phenyl organosulfonates were tolerated, and the reaction afforded coupling products with high efficiency. Excellent chemoselectivity was exhibited between halides and other groups, such as -COOH, -NO₂ , halogen, heterocyclic ring, ester, and ketone groups. The stereoselectivity suggested that the reaction mechanism might involve an organosamarium species.

Keywords: halides; homocoupling; nickel(II) chloride; organosulfonate; samarium.