Microwave-assisted rapid and sustainable synthesis of unsymmetrical azo dyes by coupling of nitroarenes with aniline derivatives.

ABSTRACT

Aromatic azo dyes are of immense commercial importance, and the development of greener routes for their synthesis is imperative due to current environmental concerns. In the present study, a microwave-assisted route has been developed for rapid and convenient synthesis of unsymmetrical azo dyes in a single step. In a metal-catalyst-free approach, an aromatic amine was used as an in situ reductant to affect its direct cross-condensation with nitroarenes to afford a variety of dispersed and water-soluble azo dyes. The electronic and substituent effects were thoroughly understood by placing suitable substituents in both nitroarenes and aniline derivatives in competitive reactions. The microwave (MW) method worked better with aniline or electron-rich aromatic amines to prepare a range of unsymmetrical azo dyes in up to 97% yields within a few minutes. The method worked well in the gram-scale synthesis of commercial dye, solvent yellow 7.