Transition metal free intramolecular selective oxidative C(sp3)–N coupling: synthesis of N-aryl-isoindolinones from 2-alkylbenzamides

Ajay Verma; Saket Patel; Meenakshi; Amit Kumar; Abhimanyu Yadav; Shailesh Kumar; Sadhan Jana; Shubham Sharma; Ch. Durga Prasad; Sangit Kumar

doi:10.1039/C4CC08717H

Transition metal free intramolecular selective oxidative C(sp³)–N coupling: synthesis of N-aryl-isoindolinones from 2-alkylbenzamides†‡

Ajay Verma,^a Saket Patel,^a Meenakshi,^a Amit Kumar,^a Abhimanyu Yadav,^a Shailesh Kumar,^a Sadhan Jana,^a Shubham Sharma,^a Ch. Durga Prasad^a and Sangit Kumar*^a

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^a Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Indore By-pass Road, Bhauri, Bhopal, Madhya Pradesh, India-462 066
E-mail: sangitkumar@iiserb.ac.in

Abstract

A synthetic method has been developed for the preparation of biologically important isoindolinones including indoprofen and DWP205190 drugs from 2-alkylbenzamide substrates by transition metal-free intramolecular selective oxidative coupling of C(sp³)–H and N–H bonds utilizing iodine, potassium carbonate and di-tert-butyl peroxide in acetonitrile at 110–140 °C.

Chemical Communications

Transition metal free intramolecular selective oxidative C(sp³)–N coupling: synthesis of N-aryl-isoindolinones from 2-alkylbenzamides†‡

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Transition metal free intramolecular selective oxidative C(sp³)–N coupling: synthesis of N-aryl-isoindolinones from 2-alkylbenzamides

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