39642-65-4Relevant articles and documents
Controlled spacing of metal atoms via ligand hydrogen bonds
Schauer,Matwey,Fowler,Lauher
, p. 10245 - 10246 (1997)
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Palladium-Catalyzed Aerobic Oxidative Carbonylation of Amines Enables the Synthesis of Unsymmetrical N,N′-Disubstituted Ureas
Zeng, Honglan,Du, Hongyan,Gong, Xu,Zhang, Jie,Han, Wei
, p. 1223 - 1226 (2021/06/02)
A ligand-free palladium-catalyzed aerobic oxidative carbonylation of amines for the synthesis of ureas, particular unsymmetrically N,N′-disubstituted ureas, which cannot be accessed by any other palladium-catalyzed oxidative carbonylation of amines to date, is presented. An array of symmetrical and unsymmetrical ureas were straightforwardly synthesized by using inexpensive, readily available, stable, and safe amines with good to excellent yields under a pressure of 1 atm. This novel method employs oxygen as the sole oxidant and offers an attractive alternative to transition-metal-based oxidant systems.
Ruthenium-Catalyzed Urea Synthesis by N-H Activation of Amines
Krishnakumar, Varadhan,Chatterjee, Basujit,Gunanathan, Chidambaram
supporting information, p. 7278 - 7284 (2017/06/23)
Activation of the N-H bond of amines by a ruthenium pincer complex operating via amine-amide metal-ligand cooperation is demonstrated. Catalytic formyl C-H activation of N,N-dimethylformamide (DMF) is observed in situ, which resulted in the formation of CO and dimethylamine. The scope of this new mode of bond activation is extended to the synthesis of urea derivatives from amines using DMF as a carbon monoxide (CO) surrogate. This catalytic protocol allows the synthesis of simple and functionalized urea derivatives with liberation of hydrogen, devoid of any stoichiometric activating reagents, and avoids the direct use of fatal CO. The catalytic carbonylation occurred at low temperature to provide the formamide; a formamide intermediate was isolated. The consecutive addition of different amines provided unsymmetrical urea compounds. The reactions are proposed to proceed via N-H activation of amines followed by CO insertion from DMF and with liberation of dihydrogen.
Selective N-methylation of aliphatic amines with CO2 and hydrosilanes using nickel-phosphine catalysts
Gonzlez-Sebastin, Lucero,Flores-Alamo, Marcos,Garca, Juventino J.
, p. 763 - 769 (2015/05/12)
A method using CO2 and PhSiH3 for the methylation of primary and secondary aliphatic amines catalyzed by Ni (0) complexes was developed, selectively producing the monomethylated products in moderate to good yields. For that purpose, two catalysts were used: [(dippe)Ni(μ-H)]2 and the commercially available Ni(COD)2/dcype, both of which were rather efficient in this process. With a slight experimental modification, the reaction allowed the production of monomethylated ureas in good yields by using low amounts of PhSiH3. On the basis of the experimental results, we propose a possible reaction mechanism for the formation of the new C-N bond.
