4.6 Article

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

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 41, Pages 8054-8058

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob01709a

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The elemental sulfur-DMSO couple efficiently promotes the oxidative coupling of active methylhetarenes with amines to yield amides under simple heating conditions. Iron, nickel, and cobalt salts, as well as other substrates, can serve as efficient catalysts for this reaction.
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.

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