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Potential N-Heterocyclic Carbene Precursors in the Palladium-Catalyzed Heck Reaction

Authors


  • Contract grant sponsor: İnönü University Research Fund.

  • Contract grant number: İÜBAP 2011/142.

Correspondence to: İsmail Özdemir; e-mail: ismail.ozdemir@inonu.edu.tr.

ABSTRACT

A novel 1-(cyclobutylmethyl)-substi-tuted imidazolidinium/benzimidazolium salts as N-heterocyclic carbene (NHC) precursors were successfully synthesized and characterized by 1H NMR, 13C NMR, IR, and elemental analysis techniques. These compounds were easily prepared from the reaction of N-alkyl imidazoline/N-alkyl benzimidazole with bromomethylcyclobutane in high yields. The in situ formed catalytic system derived from the NHC precursor and Pd(OAc)2 was used in the Heck reaction between aryl halides and styrene with potassium hydroxide in water. The corresponding Heck products were obtained in good yields. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 24:77–83, 2013; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21065

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