Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,2,3-Triazole-5-carboxamides Using Dimethyl Carbonate as Sustainable Solvent

Author(s)

de Albuquerque, Danilo Yano ^[1] ; de Moraes, Juliana R. ^[1] ; Schwab, Ricardo S. ^[1]

Affiliation

^[1] Univ Fed Sao Carlos UFSCar, Ctr Excellence Res Sustainable Chem CERSusChem, Rodovia Washington Luis, Km 235, SP310, BR-13565905 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2019, n. 39, p. 6673-6681, OCT 24 2019.
• Web of Science Citations: 0

Abstract

A simple and direct palladium-catalyzed aminocarbonylation of 5-iodo-1,2,3-triazoles backbone for the incorporation of an amide functional group is presented. The approach is based on the palladium catalyzed carbonylative coupling reaction of iodo-triazole with different amines employing formic acid and sulfuric acid as CO source (Morgan's reaction) to provide the 1,2,3-triazole-5-carboxamides in good to excellent yields. The important features of this methodology include short reaction time, high yields, the use of dimethyl carbonate as a sustainable solvent, and the use of efficient alternative source of carbon monoxide, avoiding pressurized cylinder. The methodology described herein for the synthesis of 1,4,5-trisubstituted 1,2,3-triazole-5-carboxamides, can offers an alternative path for functionalization of other heterocycles. (AU)

• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Research Centers in Engineering Program
• FAPESP's process: 13/06558-3 - Asymmetric catalysis: preparation of chiral alcohols and their derivatives from highly functionalized organozinc reagents and application of new chiral ligands supported on magnetic nanoparticles
• Grantee: Ricardo Samuel Schwab
• Support Opportunities: Regular Research Grants