Benzothiazole moieties are found in many bioactive compounds such as anticancer, antimicrobial, and antiviral molecules. Synthetic routes to access these compounds typically require high temperatures and high catalyst loading. Nucleophilic partners used for the synthesis of these moieties have been limited to amines and thiols. However, phenol nucleophilic partners have not been reported yet. Additionally, alkyl halides as electrophilic coupling partners have also not been reported. Herein we present a low loading copper-catalyzed synthesis of benzothiazole derivatives from ortho-iodoaniline, carbon disulfide, and phenol nucleophilic partners. Importantly, this method also enables the use of electrophilic partners such as alkyl iodide to generate benzothiazole derivatives. The reaction proceeds in moderate to good yields under mild conditions at room temperature with only 5 mol% catalysts. Substrate scope, mechanistic work, and functional group compatibility will be presented.

Phenols and alkyl halides as coupling partners in copper-catalyzed benzothiazoles syntheses

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