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, By Abdolkarim Zare

Research

Title	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
Type	Article
Keywords	Trityl chloride; Multi-component condensation; 1-Amido-alkyl-2-naphthol; 1-Thioamido-alkyl-2-naphthol; 1-Carbamato-alkyl-2-naphthol; Solvent-free
Journal	TETRAHEDRON
DOI	10.1016/j.tet.2012.10.042
Researchers	Ardeshir Khazaei (First researcher) , Mohammad Ali Zolfigol (Second researcher) , Ahmad Reza Moosavi-Zare (Third researcher) , Fereshteh Abi (Fourth researcher) , Abdolkarim Zare (Fifth researcher) , Hamideh Kaveh (Not in first six researchers) , Vahid Khakyzadeh (Not in first six researchers) , Masoud Kazem-Rostami (Not in first six researchers) , Abolfath Parhami (Not in first six researchers) , Hossein Torabi-Monfared (Not in first six researchers)

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.