Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media

Ardeshir Khazaei*, Mohammad Ali Zolfigol, Ahmad Reza Moosavi-Zare, Fereshteh Abi, Abdolkarim Zare, Hamideh Kaveh, Vahid Khakyzadeh, Masoud Kazem-Rostami, Abolfath Parhami, Hossein Torabi-Monfared

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

67 Citations (Scopus)

Abstract

Trityl chloride (TrCl), efficiently catalyzes the one-pot multi-component condensation of β-naphthol with aromatic aldehydes and amides/thioamides/ carbamates such as acetamide, benzamide, nicotinamide, thioacetamide, and methylcarbamate under solvent-free and neutral conditions to afford 1-amido-alkyl-2-naphthols, 1-thioamido-alkyl-2-naphthols, and 1-carbamato-alkyl-2-naphthols in high yields and very short reaction times. Mechanistically, it is interesting that trityl chloride through the in situ generation of trityl carbocation with inherent instability is efficient as a reusable homogeneous organocatalyst in neutral media.

Original languageEnglish
Pages (from-to)212-218
Number of pages7
JournalTetrahedron
Volume69
Issue number1
DOIs
Publication statusPublished - 7 Jan 2013
Externally publishedYes

Keywords

  • 1-Amido-alkyl-2-naphthol
  • 1-Carbamato-alkyl-2-naphthol
  • 1-Thioamido-alkyl-2-naphthol
  • Multi-component condensation
  • Solvent-free
  • Trityl chloride

Fingerprint

Dive into the research topics of 'Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media'. Together they form a unique fingerprint.

Cite this