Synthesis of 2‐Aminobenzothiazoles via Copper(I)‐Catalyzed Cross‐Coupling with Part‐Per‐Million Catalyst Loadings

Abstract

An efficient protocol has been developed for the preparation of 2-aminobenzothiazoles via a copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates at very low catalyst loadings [typically 50 ppm of copper(I) iodide (CuI)]. A variety of 2-iodoanilines could be cross-coupled with isothiocyanates, affording 2-aminobenzothiazoles in moderate to good yields (49-93%) under the given conditions. The turnover number (TON) of this reaction reaches 67,000 and the reaction could be scaled up, at least, to the gram-scale.

Design and Synthesis of a Class of Twin‐Chain Amphiphiles for Self‐Assembled Monolayer‐Based Electrochemical Biosensor Applications

“…N ‐Butylbenzo[ d ]thiazol‐2‐amine (3c): Colorless solid. Characterization data were identical with the reported data 21…”

Convenient and Reliable Routes Towards 2‐Aminothiazoles: Palladium‐Catalyzed versus Copper‐Catalyzed Aminations of Halothiazoles

“…Characterization data were identical with the reported data. [21] N-Isopentylbenzo[d]thiazol-2-amine (3d): Orange solid. Characterization data were identical with the reported data.…”

A practical synthesis of 2-aminobenzothiazoles via the tandem reactions of 2-haloanilines with isothiocyanates catalyzed by immobilization of copper in MCM-41

“…1 (110) and (200) with lower intensities were also detected, and therefore the chemical bonding procedure did not diminish the structural ordering of the MCM- 41 …”