Electrochemical Amidation: Benzoyl Hydrazine/Carbazate and Amine as Coupling Partners

Tipu Alam, Amitava Rakshit, Hirendra Nath Dhara, Angshuman Palai and Bhisma K. Patel*

*Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati 781039, India, Email: pateliitg.ac.in

T. Alam, A. Rakshit, H. N. Dhara, A. Palai, B. K. Patel, Org. Lett., 2022, 24, 6619-6624.

DOI: 10.1021/acs.orglett.2c02626

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Abstract

An electrochemical amidation of benzoyl hydrazine/carbazate and primary/secondary amine as coupling partners proceeds under metal-free and exogenous oxidant-free conditions produces only N₂ and H₂ as byproducts. Mechanistic studies reveal the in situ generations of both acyl and N-centered radicals.

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proposed mechanism

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Key Words

amides,  electrochemistry

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ID: J54-Y2022