TBAF-assisted copper-catalyzed N-arylation and benzylation of benzazoles with aryl and benzyl halides under the ligand/base/ solvent-free conditions.

J Org Chem

Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Sciences, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University, Jinju 660-701, Korea.

Published: August 2009

AI Article Synopsis

  • TBAF-assisted N-arylation and benzylation reactions involve using benzazoles like 1H-benzimidazole and 1H-indole with aryl and benzyl halides.
  • The reactions occur successfully in the presence of CuBr2 without any additional ligands, bases, or solvents.
  • The process yields moderate to good results, showcasing an efficient way to modify these aromatic compounds.

Article Abstract

TBAF-assisted N-arylation and benzylation of benzazoles such as 1H-benzimidazole, 1H-indole, and 1H-benzotriazole with aryl and benzyl halides have been demonstrated under the ligand/base/solvent-free conditions. In the presence of CuBr2 and TBAF (n-Bu4NF), the azoles underwent N-arylation and benzylation with aryl and benzyl halides smoothly in moderate to good yields. It is noteworthy that the reaction is conducted under the ligand/base/solvent-free conditions.

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http://dx.doi.org/10.1021/jo900752zDOI Listing

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