A simple and efficient oxidation of primary and secondary benzylamines to acids using table salt in aqueous medium. (19th November 2021)

• Record Type: Journal Article
• Authors: Kushawaha, Ajay Kishor; Jaiswal, Arvind Kumar; Pandey, Shubham; Sashidhara, Koneni V.
• Is Part Of: Tetrahedron. Volume 101(2021)
• Publication Date: 2021-11-19
• Subjects: Transition metal free -- Eco-friendly -- Efficient -- Sodium chloride -- Terephthalic acid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132502
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Herein, we have developed a novel, simple, efficient method for the oxidation of aromatic benzylamines to corresponding acids using common table salt in aqueous medium. Oxidation of benzylamine was achieved by using NaCl (20 mol%) as a catalyst, NaOH (4 equiv) and TBHP (5 equiv) as oxidant, in moderate to good yields (34–84%). Control experiments revealed that in situ generated ClO2 − ion is the active form of the catalyst. This methodology can also be scaled up for easy accessibility to the industrially important terephthalic acid as well. This investigation provided a facile entry of various primary as well as secondary benzylamines with wide range of functional group tolerance. Graphical abstract: Image 1