1796-27-6Relevant articles and documents
Group 3 metal (Sc, La) triflates as catalysts for the carbomethoxylation of aliphatic amines with dimethylcarbonate under mild conditions
Distaso, Monica,Quaranta, Eugenio
, p. 1531 - 1539 (2004)
The activity of Sc(OTf)3 and La(OTf)3 (OTf=SO 3CF3) as catalysts for the phosgene-free synthesis of carbamate esters via carbomethoxylation of aliphatic amines with dimethylcarbonate (DMC) has been investigated. In the presence of M(OTf) 3 (M=Sc, La), primary and secondary aliphatic amines easily react with dimethylcarbonate, under very mild conditions (20°C), to afford carbamate esters with good yield and excellent selectivity (?100%). Sc(OTf)3 is a more effective catalyst than the homologue La salt. The carbomethoxylation reaction requires as strict anhydrous conditions, as, at 20°C, the presence of water inhibits markedly the catalytic activity of both triflate salts. Temperature influences carbamate selectivity, which is lower at higher temperature because of deleterious formation of N-methylation side-products.
Copper-Catalyzed Coupling of Amines with Carbazates: An Approach to Carbamates
Wang, Song-Ning,Zhang, Guo-Yu,Shoberu, Adedamola,Zou, Jian-Ping
, p. 9067 - 9075 (2021/07/19)
A new approach for the preparation of carbamatesviathe copper-catalyzed cross-coupling reaction of amines with alkoxycarbonyl radicals generated from carbazates is described. This environmentally friendly protocol takes place under mild conditions and is compatible with a wide range of amines, including aromatic/aliphatic and primary/secondary substrates.
Electrochemical Functional-Group-Tolerant Shono-type Oxidation of Cyclic Carbamates Enabled by Aminoxyl Mediators
Wang, Fei,Rafiee, Mohammad,Stahl, Shannon S.
supporting information, p. 6686 - 6690 (2018/05/07)
An electrochemical method has been developed for α-oxygenations of cyclic carbamates by using a bicyclic aminoxyl as a mediator and water as the nucleophile. The mediated electrochemical process enables substrate oxygenation to proceed at a potential that is approximately 1 V lower than the redox potential of the carbamate substrate. This feature allows for functional-group compatibility that is inaccessible with conventional Shono oxidations, which proceed by direct electrochemical substrate oxidation. This reaction also represents the first α-functionalization of non-activated cyclic carbamates with oxoammonium oxidants.
L-Proline-TBAB-catalyzed phosgene free synthesis of methyl carbamates from amines and dimethyl carbonate
Kumar, Subodh,Jain, Suman L.
, p. 2935 - 2938 (2013/09/12)
The reaction of amines and dimethyl carbonate (DMC) in the presence of catalytic amounts of l-proline and tetrabutylammonium bromide (TBAB) afforded methyl carbamates in good to excellent yields under mild conditions. The presence of both l-proline and TBAB co-catalysts is vital for this transformation.
