Litcius/Paper detail

Sulfur–DMSO promoted oxidative coupling of active methylhetarenes with amines: access to amides

Thi Thu Tram Nguyen, Thi Thu Tram Nguyen, Viêt Dung Duong, Thi Ngoc Nga Pham, Quoc Thanh Duong, Thanh Bình Nguyễn, Thanh Bình Nguyễn

2022Organic & Biomolecular Chemistry11 citationsDOIOpen Access PDF

Abstract

The elemental sulfur-DMSO couple was found to efficiently promote the oxidative coupling of active methylhetarenes with amines to yield amides under simple heating conditions. When 2-methylquinoline was used as the methylhetarene component, the formation of the expected 2-quinolinecarboxamides from anilines could be efficiently catalyzed by iron, nickel and cobalt salts. The method displayed good functional group tolerance and was applicable to aromatic, heteroaromatic and aliphatic amines. Other substrates such as phenylacetic acid, dibenzyl disulfide, and benzylamine could act as competent partners in place of methylhetarenes.

Topics & Concepts

SulfurYield (engineering)ChemistryOxidative coupling of methaneOxidative phosphorylationCatalysisCoupling reactionCoupling (piping)Component (thermodynamics)Combinatorial chemistryOrganic chemistryPolymer chemistryMaterials scienceBiochemistryMetallurgyPhysicsThermodynamicsChemical Synthesis and AnalysisSulfur-Based Synthesis TechniquesAdvanced Synthetic Organic Chemistry