Ortho-selective direct cross-coupling reaction of 2-aryloxazolines and 2-arylimidazolines with aryl and alkenyl halides catalysed by ruthenium complexes

Shuichi Oi, Emi Aizawa, Yukako Ogino, Yoshio Inoue

Research output: Contribution to journalArticle

163 Citations (Scopus)

Abstract

(Chemical Equation Presented) The ortho position of the aromatic ring in 2-aryloxazolines and 2-arylimidazolines is selectively arylated and alkenylated with organic halides in the presence of a ruthenium(II)-phosphine complex. In the case of unsubstituted and para-substituted phenyloxazolines, 1:2 coupled products were obtained preferentially, while 1:1 coupled products were obtained in the case of meta-substituted phenyloxazolines and N-acylarylimidazolines. The reaction is proposed to proceed via the generation of an organoruthenium intermediate, formed by oxidative addition of the organic halide, and ortho-ruthenation directed by the coordination of the 2-oxazolinyl or 2-imidazolinyl group to the ruthenium center.

Original languageEnglish
Pages (from-to)3113-3119
Number of pages7
JournalJournal of Organic Chemistry
Volume70
Issue number8
DOIs
Publication statusPublished - 2005 Apr 15

ASJC Scopus subject areas

  • Organic Chemistry

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