120982-35-6Relevant academic research and scientific papers
Pd-Catalyzed Carbonylation of Acyl Azides
Chang, Wenxu,Fu, Bin,Huang, Baoliang,Jiao, Lei,Li, Zongyang,Wang, Peng,Xu, Shiyang,Yuan, Chenhui,Zhang, Zhenhua
, p. 9497 - 9508 (2019/08/26)
Pd-catalyzed reactions of azides with CO to access an isocynate intermediate have been developed extensively in recent years. However, the catalytic carbonylation of sensitive acyl azides has not been reported. Herein, we report a simple Pd-catalyzed carbonylation reaction of acyl azides with broad substrate scope, high efficiency, and simple operation under mild conditions, which provides facile access to acyl ureas. In addition, a mechanistic study was carried out by both experiment and DFT calculation. Control experiments and kinetic study revealed that the real active palladium species were Pd(0). The result of kinetic study suggested that palladium catalyst, azide, and CO were all involved in the turnover-limiting step except for amine. Further DFT study suggested that an unprecedented five-membered palladacycle intermediate was the key intermediate in the carbonylation reaction. ?
Palladium-catalyzed N -acylation of monosubstituted ureas using near-stoichiometric carbon monoxide
Bjerglund, Klaus,Lindhardt, Anders T.,Skrydstrup, Troels
experimental part, p. 3793 - 3799 (2012/06/04)
The palladium-catalyzed carbonylation of urea derivatives with aryl iodides and bromides afforded N-benzoyl ureas (20 examples) in yields attaining quantitative via the application of near-stoichiometric amounts of carbon monoxide generated from the decarbonylation of the CO precursor, 9-methylfluorene-9-carbonyl chloride. The synthetic protocol displayed good functional group tolerance. The methodology is also highly suitable for 13C isotope labeling, which was demonstrated through the synthesis of three benzoyl ureas, including the insecticide triflumuron, whereby 13CO was incorporated into the core structure.
