Iron(III)-catalyzed synthesis of selenoesters from α-amino carbonyl derivatives at room temperature. Issue 43 (25th October 2019)

• Record Type: Journal Article
• Authors: Chatterjee, Rana; Mukherjee, Anindita; Santra, Sougata; Zyryanov, Grigory V.; Majee, Adinath
• Is Part Of: Tetrahedron. Volume 75:Issue 43(2019)
• Publication Date: 2019-10-25
• Subjects: Selenoesters -- α-amino carbonyl -- Iron catalyst -- Room temperature -- Radical pathway; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.130624
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An Fe(III)-catalyzed efficient method has been developed for the synthesis of selenoester derivatives in high yields through the coupling of α-amino carbonyl/glycine derivatives and diselenides under ambient air. A library of benzoselenoate derivatives having a variety of substituents has been synthesized. A plausible reaction pathway has been predicted. Experimental results suggest that the reaction proceeds through a radical pathway. Operational simplicity, compatibility with various α-amino carbonyls and diselenides, high yields, fast reaction and mild reaction conditions are the notable advantages of this procedure. We have also shown the practical application of the synthesized selenoesters which is useful to generate peptide bonds in biological sciences. Graphical abstract: Image 1 Highlights: This work describes the synthesis of selenoester derivatives in high yields. FeCl3 is found to be highly effective catalyst for the synthesis of selenoesters. Coupling of α-amino carbonyl derivatives and diselenides gave the selenoesters. Experimental results suggest that the reaction proceeds through radical pathway.