1461-81-0Relevant articles and documents
A new practical method for the synthesis of unsymmetrical ureas via high-pressure-promoted condensation of 2,2,2-trichloroethyl carbamates (Troc-carbamates) with amines
Azad, Saleha,Kumamoto, Koji,Uegaki, Kaoru,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
, p. 587 - 590 (2006)
A new practical method for the synthesis of unsymmetrical ureas was achieved by condensation between 2,2,2-trichloroethyl carbamates (Troc-carbamates) and primary or secondary amines under high-pressure conditions.
Iron(II)-Catalyzed Hydroamination of Isocyanates
South, Amy J.,Geer, Ana M.,Taylor, Laurence J.,Sharpe, Helen R.,Lewis, William,Blake, Alexander J.,Kays, Deborah L.
supporting information, p. 4115 - 4120 (2019/10/17)
A two-coordinate Fe(II) m-terphenyl complex acts as a precatalyst for the hydroamination of isocyanates, affording urea and biuret derivatives, with product selectivity accomplished via modification of the reaction conditions. Using a more nucleophilic amine facilitates the insertion of up to four isocyanates into the N-H bond, affording triuret and tetrauret derivatives.
2-Picolylamino(diphenylphosphinoselenoic)amide supported zinc complexes: Efficient catalyst for insertion of N–H bond into carbodiimides, isocyanates, and isothiocyanate
Harinath, Adimulam,Bano, Kulsum,Ahmed, Shakil,Panda, Tarun K.
supporting information, p. 23 - 32 (2017/09/25)
We report here the hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by zinc complexes supported by the ligand 2-picolylamino-(diphenylphosphinoselenoic)amide [{(Ph2P-(?Se)}2NCH2(C5H4N)] (1). A series of zinc complexes [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnX2] [(X?Cl (2), Br (3a), I (4)] were prepared from ligand 1 and the corresponding zinc dihalide in a 1:1 molar ratio at 60°C in a chloroform solvent. The reaction of ligand 1 and ZnBr2 in methanol yielded another zinc complex [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnBr2(CH3OH)] (3b). The molecular structures of compounds 3a, 3b, and 4 were established through single-crystal X-ray diffraction analyses. The solid-state structures of all the complexes revealed a κ2- chelation through pyridine nitrogen and selenium atoms of ligand 1 to the zinc ion. Complex 2 proved to be a competent pre-catalyst for the addition of the amine N–H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanate and phenylisothiocyanate in toluene solvents, which proceeded rapidly at room temperature with 5 mol% catalyst loading to yield (up to 99%) the corresponding derivatives of urea and thio-urea. However, a temperature of 90°C was needed for the hydroamination of N,N′ dicyclohexylcarbodiimide. We also report the most plausible mechanism of the hydroamination reaction.