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

Research output: Contribution to journalArticle

65 Citations (Scopus)

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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Bearings (structural)
Phosphines
Imidazoles
Microwave irradiation
carbenes
imidazoles
phosphines
Chlorides
palladium
Salts
chlorides
Ligands
Derivatives
Electrons
Substrates
chlorobenzenes
metathesis
halides
acetates
salts

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Kumar, P. Vijaya ; Lin, Wu Shien ; Shen, Jiun Shian ; Nandi, Debkumar ; Lee, Hon Man. / Direct C5-arylation reaction between imidazoles and aryl chlorides catalyzed by palladium complexes with phosphines and N-heterocyclic carbenes. In: Organometallics. 2011 ; Vol. 30, No. 19. pp. 5160-5169.
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Direct C5-arylation reaction between imidazoles and aryl chlorides catalyzed by palladium complexes with phosphines and N-heterocyclic carbenes. / Kumar, P. Vijaya; Lin, Wu Shien; Shen, Jiun Shian; Nandi, Debkumar; Lee, Hon Man.

In: Organometallics, Vol. 30, No. 19, 10.10.2011, p. 5160-5169.

Research output: Contribution to journalArticle

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AU - Kumar, P. Vijaya

AU - Lin, Wu Shien

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AU - Nandi, Debkumar

AU - Lee, Hon Man

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