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Reductive Homocoupling of Organohalides Using Nickel(II) Chloride and Samarium Metal
Author(s) -
Liu Yongjun,
Xiao Shuhuan,
Qi Yan,
Du Feng
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201601712
Subject(s) - chemoselectivity , chemistry , halide , aryl , ketone , medicinal chemistry , alkyl , samarium , catalysis , nickel , halogen , ring (chemistry) , coupling reaction , combinatorial chemistry , polymer chemistry , organic chemistry
A homocoupling method for organohalides and organosulfonates promoted by samarium metal and HMPA, and catalyzed by NiCl 2 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, −NO 2 , halogen, heterocyclic ring, ester, and ketone groups. The stereoselectivity suggested that the reaction mechanism might involve an organosamarium species.