25348-08-7Relevant articles and documents
Zinc Powder Catalysed Formylation and Urealation of Amines Using CO2 as a C1 Building Block?
Du, Chongyang,Chen, Yaofeng
, p. 1057 - 1064 (2020/06/30)
Transformation of CO2 into valuable organic compounds catalysed by cheap and biocompatible metal catalysts is one of important topics of current organic synthesis and catalysis. Herein, we report the zinc powder catalysed formylation and urealation of amines with CO2 and (EtO)3SiH under solvent free condition. Using 2 molpercent zinc powder as the catalyst, a series of secondary amines, both the aromatic ones and the aliphatic ones, can be formylated into formamides. When primary aromatic amines were used as the substrates, the reactions produce urea derivatives. The electronic and steric effects from the substrates on the formylation and urealation reactions were observed and discussed. The recovery and reusability of zinc powder were investigated, showing the zinc powder can be reused in the formylation reaction without loss of catalytic activity. The analysis on the reactants/products mixture after filtering out the zinc powder showed the zinc concentration in the mixture is low to 1 ppm. The pathways for the formylation and urealation of amines with this catalytic system were also investigated, and related to the different substrates.
Synthesis of Urea Derivatives from CO2 and Silylamines
Xu, Maotong,Jupp, Andrew R.,Ong, Maegan S. E.,Burton, Katherine I.,Chitnis, Saurabh S.,Stephan, Douglas W.
, p. 5707 - 5711 (2019/04/16)
A series of thirty-three N,N′-diaryl, dialkyl, and alkyl-aryl ureas have been prepared in pyridine or toluene by reaction of silylamines with CO2. This protocol is shown to provide facile access to 13C-labeled ureas, as well as chiral and macrocyclic ureas. These reactions proceed through initial generation of the corresponding silylcarbamates, which subsequently react with silylamine under thermal conditions to afford the thermodynamically favored urea and disilyl ether.
Cobalt/rhodium heterobimetallic nanoparticle-catalyzed oxidative carbonylation of amines in the presence of carbon monoxide and molecular oxygen to ureas
Park, Ji Hoon,Yoon, Jae Chun,Chung, Young Keun
supporting information; experimental part, p. 1233 - 1237 (2009/12/07)
An environmentally friendly oxidative carbonylation of aliphatic and aromatic primary amines to ureas has been successfully achieved in the presence of a catalytic amount of cobalt/rhodium heterobimetallic nanoparticles without any promoters. The catalyst system could be reused with only a slight loss of catalytic activity.
N-heterocyclic carbene - Palladium complexes as efficient catalysts for the oxidative carbonylation of amines to ureas
Zheng, Shuzhan,Peng, Xingao,Liu, Jianming,Sun, Wei,Xia, Chungu
, p. 1471 - 1476 (2008/02/09)
A highly efficient oxidative carbonylation reaction of amines to ureas was developed making use of carbene-palladium complexes in the absence of any promoter. Both aliphatic amines and aromatic amines were transformed in good to excellent yields to the expected ureas.
Ruthenium catalysed N,N'-Diarylurea Synthesis from N-Aryl substituted Formamides and Aminoarenes
Kotachi, Shinji,Tsuji, Yasushi,Kondo, Teruyuki,Watanabe, Yoshihisa
, p. 549 - 550 (2007/10/02)
N-Aryl substituted formamides react smoothly with aminoarenes in the presence of a catalytic amount of dichlorotris(triphenylphosphine)ruthenium to afford various N,N'-diarylureas in good yields.
ANIONIC ACTIVATION BY FLUORIDE ION IN SOLID-LIQUID SYSTEMS. SYNTHESIS OF 3 (2H)-FURANONES AND 2 (5H)-FURANONES.
Sebti, S.,Foucaud, A.
, p. 1361 - 1368 (2007/10/02)
The evolution of 2-acyloxy 2-methyl 3-oxobutanamides 1 and 2-acyloxy 3-oxo 2,3-diphenylpropanamides 13 under anionic activation by cesium fluoride was studied.The fluoride ion is an efficient base for the heterocyclization of 1 into 3 (2H)-furanones and 2 (5H)-furanones, but the hydrolysis of the ester group lowered the selectivity of the reaction.However, the cleavage of 13 into the esters 14 and the cyclization of 3-benzoyloxy 3-methyl 2-butanone into bullatenone are very selective.
