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Pd/C‐Catalyzed Domino Synthesis of Urea Derivatives Using Chloroform as the Carbon Monoxide Source in Water
Author(s) -
Wang Liang,
Wang Hao,
Li Guiqing,
Min Shuliang,
Xiang Fangyuan,
Liu Shiqi,
Zheng Waigang
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800954
Subject(s) - chemistry , sodium azide , catalysis , carbonylation , carbon monoxide , aryl , chloroform , nucleophile , urea , domino , curtius rearrangement , organic chemistry , medicinal chemistry , alkyl
A Pd/C‐catalyzed domino synthesis of symmetrical and unsymmetrical ureas from aryl iodides, sodium azide, amines and CHCl 3 in water has been developed. This reaction proceeds with sequential carbonylation, Curtius rearrangement and nucleophilic addition. CHCl 3 serves as a convenient and safe alternation of CO gas in the presence of KOH. A series of urea derivatives were obtained in moderate to good yields with good functional group tolerance. Furthermore, the Pd/C catalyst could be readily recovered with slight decrease in the catalytic activity after six consecutive runs.