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Palladium‐Catalyzed Aminocarbonylation Reaction to Access 1,2,3‐Triazole‐5‐carboxamides Using Dimethyl Carbonate as Sustainable Solvent
Author(s) -
Albuquerque Danilo Yano,
Moraes Juliana R.,
Schwab Ricardo S.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901249
Subject(s) - chemistry , palladium , amide , catalysis , carbonylation , 1,2,3 triazole , sulfuric acid , solvent , formic acid , combinatorial chemistry , organic chemistry , dimethyl carbonate , carbon monoxide
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.