Metal‐Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho‐Carbonyl Anilines. Issue 29 (4th August 2021)

• Record Type: Journal Article
• Authors: Garia, Alankrita; Grover, Jatin; Jain, Nidhi
• Is Part Of: European journal of organic chemistry. Issue 29(2021)
• Page Start: 4125
• Page End: 4131
• Publication Date: 2021-08-04
• Subjects: Heterocyclization -- Iminoiodane -- Iodosyl benzene -- Metal-free -- Nitrene -- ortho-Carbonyl anilines; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100756
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Here, we report a metal‐free synthesis of anthranils from ortho ‐carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in‐situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho ‐carbonyl aniline on nitrene results in heterocyclization. Abstract : A metal‐free synthesis of anthranils from ortho ‐carbonyl anilines using PhIO as a sole reagent under ambient conditions is described. No external additives are required, the reaction has broad substrate scope and delivers anthranils in excellent yields via oxidative heterocyclization.