Direct Synthesis of Paracetamol via Site-Selective Electrochemical Ritter-type C-H Amination of Phenol

Irshad Maajid Taily, Debarshi Saha and Prabal Banerjee*

*Department of Chemistry, Indian Institute of Technology Ropar, Lab no. 406, S. S. Bhatnagar Block, Rupnagar, Punjab 140001, India, Email: prabaliitrpr.ac.in

I. M. Taily, D. Saha, P. Banerjee, Org. Lett., 2022, 24, 2310-2314.

DOI: 10.1021/acs.orglett.2c00439

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Abstract

A regioselective electrochemical Ritter-type reaction at the C(sp²)-H of unprotected phenol enables an environmentally benign and direct synthesis of paracetamol. The reaction proceeds under exogenous oxidant- and catalyst-free conditions. The protocol is scalable and can be deployed to a variety of phenols.

see article for more examples

proposed mechanism

Commercial routes for paracetamol production

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Key Words

Ritter reaction, anilines

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ID: J54-Y2022