Mechanism of substitution reaction on sp2-carbon center with lithium organocuprate

Naohiko Yoshikai, Eiichi Nakamura

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)


Theory and experiments suggest that the substitution reaction of a lithium dialkylcuprate(I) with an alkenyl bromide takes place through a π-complex (cuprio(III)cyclopropane) that directly breaks down to the alkenylated product rather than via a conventional three-centered transition state. This mechanism is consistent with the broader mechanistic picture of the organocuprate reactions and accounts for the retentive stereochemistry and the kinetic isotope effect observed in the experiments.

Original languageEnglish
Pages (from-to)12264-12265
Number of pages2
JournalJournal of the American Chemical Society
Issue number39
Publication statusPublished - 2004 Oct 6


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