Efficient Non‐Catalytic Carboxylation of Diamines to Cyclic Ureas Using 2‐Pyrrolidone as a Solvent and a Promoter

Carboxylation reactions of diamines were found to proceed rapidly and non‐catalytically, producing corresponding cyclic ureas in excellent yields and selectivities when 2‐pyrrolidone (2‐PY) was used as a solvent. A similar promoting effect with 2‐PY was also observed for the carboxylation of monoami...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-01, Vol.361 (2), p.297-306
Main Authors: Hwang, Junhyeok, Han, Donggu, Oh, Jin Joo, Cheong, Minserk, Koo, Hyun‐Joo, Lee, Je Seung, Kim, Hoon Sik
Format: Article
Language:English
Subjects:
Amines
Carbon dioxide
Carboxylation
Catalysis
CO2 utilization
Cyclic ureas
Diamines
Hydrogen bonding
Solvents
Tautomerization
Ureas
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Summary:Carboxylation reactions of diamines were found to proceed rapidly and non‐catalytically, producing corresponding cyclic ureas in excellent yields and selectivities when 2‐pyrrolidone (2‐PY) was used as a solvent. A similar promoting effect with 2‐PY was also observed for the carboxylation of monoamines by carbon dioxide (CO2). Most notably, the carboxylation reactions of mono‐ and diamines conducted in 2‐PY afforded 2–4 times higher yields of corresponding dialkyl ureas and cyclic ureas compared with those in N‐methyl‐2‐pyrrolidone (NMP). Such a dramatic promoting effect using 2‐PY is believed to be associated with the multiple hydrogen bonding interactions between 2‐PY and the CO2‐containing species of amines. Due to such favorable interactions, carboxylation reactions seem to be more facilitated in 2‐PY than in NMP.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800945