Copper-catalyzed amidation of benzoic acids using tetraalkylthiuram disulfides as amine sources

ABSTRACT

A facile method for the copper-catalyzed synthesis of N-substituted benzamides was explored. In the presence of CuBr and di-tert-butyl peroxide, various N-substituted benzamides were prepared through amidation of benzoic acid by using commercially available and cheap tetraalkylthiuram disulfides as amine sources. With this protocol, a series of 14 N-substituted benzamides were furnished in good to excellent yields. The broad substrate scope and good to excellent yield show its practical synthetic value in organic synthesis.

GRAPHICAL ABSTRACT

KEYWORDS:

• Amidation
• benzamide
• copper bromide
• di-tert-butyl peroxide
• tetraalkylthiuram disulfide

Acknowledgments

We thank the foundation support from National Natural Science Foundation of China (21302150), Hubei Provincial Department of Education (D20131501), Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry [2012]1707 and foundation of High-end Talent Cultivation Program from Wuhan Institute of Technology. We also thank Prof. AiwenLei at Wuhan University for his generous NMR analysis support.