K3PO4-catalyzed carboxylation of amines to 1,3-disubstituted ureas: A mechanistic consideration

•Synthesis of 1,3-disubstituted ureas by the carboxylation of amines with CO2.•K3PO4 as benign catalyst for the carboxylation of amines.•Mechanistic and computational investigations on the reactive species.•K3PO4 was transformed into KH2PO4 and KHCO3 in the presence of CO2 and water. K3PO4 was found...

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Bibliographic Details
Published in:Applied catalysis. B, Environmental Environmental, 2014-01, Vol.144, p.317-324
Main Authors: Choi, Young-Seop, Kim, Heehwan, Shin, Seung Hoon, Cheong, Minserk, Kim, Yong Jin, Jang, Ho Gyeom, Kim, Hoon Sik, Lee, Je Seung
Format: Article
Language:English
Subjects:
Amines
Carbon dioxide
Carboxylation
Catalysis
Chemistry
Computation
Diffraction
Exact sciences and technology
General and physical chemistry
K3PO4
Substituted ureas
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Ureas
X-rays
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Summary:•Synthesis of 1,3-disubstituted ureas by the carboxylation of amines with CO2.•K3PO4 as benign catalyst for the carboxylation of amines.•Mechanistic and computational investigations on the reactive species.•K3PO4 was transformed into KH2PO4 and KHCO3 in the presence of CO2 and water. K3PO4 was found to effectively catalyze the carboxylation of amines by CO2, producing corresponding 1,3-disubstituted ureas in high yields and selectivities. X-ray diffraction and FT-IR spectroscopic analysis of the solid mixture, recovered from the carboxylation of n-butylamine, revealed that K3PO4 was completely transformed into KH2PO4 and KHCO3. Mechanistic and computational studies suggested that the high activity of K3PO4 could be attributed to the synergy effect exerted by the co-presence of KHCO3 and KH2PO4, generated from the interaction of K3PO4 with CO2 and water.
ISSN:0926-3373
1873-3883
DOI:10.1016/j.apcatb.2013.07.017