Direct C5-arylation reaction between imidazoles and aryl chlorides catalyzed by palladium complexes with phosphines and N-heterocyclic carbenes

P. Vijaya Kumar, Wu Shien Lin, Jiun Shian Shen, Debkumar Nandi, Hon Man Lee

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Abstract

Palladium(II) acetate complexes bearing phosphines and carbene ligands, Pd(L)(PR3)(OAc)2 (1a, R = Ph; 1b, R = Cy; L = 1,3-dibenzylimidazol-2-ylidene), were prepared by salt metathesis reactions of their chloro complexes with AgOAc in good yields. The electron-rich 1b was efficient in catalyzing C-5 direct arylation of imidazoles with aryl halides. Most significantly, the catalytic system allows a range of aryl chlorides as substrates. Microwave irradiation effectively promotes the reactions, with good yields obtainable in only 2 h. In combination with the classical method of C-C bond formation reactions, novel imidazole derivatives featuring biaryl and styryl subunits were successfully obtained from 1,4-dichlorobenzene and 1-bromo-4-chlorobenzene.

Original languageEnglish
Pages (from-to)5160-5169
Number of pages10
JournalOrganometallics
Volume30
Issue number19
DOIs
Publication statusPublished - 2011 Oct 10

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All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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