2,2′-Azobenzothiazole as a New Recyclable Oxidant for Heterogeneous Thiocyanation of Aromatic Compounds with Ammonium Thiocyanate

Abstract

A simple synthesis of thiocyanated aromatics has been developed by using heteroaromatic azo compounds such as 2,2′-azobenzothiazole as a mild and heterogeneous oxidant. The reactions proceed at room temperature with good regioselectivity. The hydrazine by-product can be easily separated by filtration and recycled for further use.

GRAPHICAL ABSTRACT

Keywords:

• Aromatic compounds
• azobenzothiazole
• heterogeneous
• thiocyanation

ACKNOWLEDGMENTS

We are thankful to the Organization of Management and Planning of Iran and Shiraz University Research Council for the partial financial support of this work.

Notes

^a Isolated yields.

^a Molar ratio of arene: A6:NH₄SCN was 1:1.9:3.

^b All the products are known compounds and were identified from their spectral data and comparison with known samples.

^c Isolated yields.

^d After 18 h, the bis-adduct was obtained in 12% yield.