Regioselective Thiocyanation of Aromatic and Heteroaromatic Compounds Using [2-(Sulfooxy)‎ethyl]sulfamic Acid as an Efficient, Recyclable Organocatalyst and Novel Difunctional Brønsted Acid

Abstract EN

A green and simple procedure for the thiocyanation of aromatic and heteroaromatic compounds is described.

[2-(Sulfooxy)ethyl]sulfamic acid (SESA) (supported on silica) is easily produced by addition of chlorosulfonic acid to 2-aminoethanol and this catalyst is applied as an efficient, reusable, and heterogeneous catalyst for the thiocyanation of heterocycles, substituted anilines (electron-rich and electron-deficient), and N,N-disubstituted aromatic amines using hydrogen peroxide in the water : ethanol as a solvent at room temperature.

The catalyst can be easily recovered and reused for five reaction cycles without considerable loss of activity.