86065-10-3Relevant articles and documents
Carbamate as an accelerating group in intermolecular Pauson-Khand reaction
Asano, Shota,Itto-Nakama, Kaori,Arimoto, Hirokazu
, (2020)
The Pauson-Khand reaction (PKR) is a powerful means for the construction of cyclopentenones. However, its applications have been limited to the intramolecular version of this reaction because poor yield and regioselectivity are often the major problems in intermolecular PKR. Here we describe that a carbamate moiety in alkene substrate accelerates this intermolecular PKR. The reaction of N-4-dimethylaminophenyl O-allyl carbamate with alkyne-cobalt complex gave cyclopentenones in high yield (up to 90%) and regioselectivity (>9:1).
Intramolecular Aminoazidation of Unactivated Terminal Alkenes by Palladium-Catalyzed Reactions with Hydrogen Peroxide as the Oxidant
Beccalli, Egle M.,Broggini, Gianluigi,Foschi, Francesca,Lo Presti, Leonardo,Loro, Camilla,Oble, Julie,Poli, Giovanni,Sala, Roberto
supporting information, (2020/02/28)
The palladium-catalyzed aminoazidation of aminoalkenes yielding azidomethyl-substituted nitrogen-containing heterocycles was developed. The procedure requires oxidative conditions and occurs at room temperature in the presence of hydrogen peroxide and NaN3 as the azide source. These conditions provide selective exo-cyclization/azidation of the carbon-carbon double bond, furnishing a versatile approach toward five-, six-, and seven-membered heterocyclic rings.
CaI2-Catalyzed direct transformation of: N -Alloc-, N -Troc-, and N -Cbz-protected amines to asymmetrical ureas
Tran, Van Hieu,Kim, Hee-Kwon
, p. 14093 - 14101 (2019/09/18)
A novel and facile CaI2-catalyzed direct synthesis of asymmetrical ureas from N-Alloc-, N-Troc-, and N-Cbz-protected amines is developed. In this study, the efficient reaction of Alloc-, Troc-, and Cbz-carbamates with amines in the presence of catalytic CaI2 successfully generated various asymmetrical ureas. This catalytic synthetic procedure provided the desired ureas via reactions of these protected aromatic and aliphatic amines with various amines in high yields without side products. This suggests that novel direct synthesis of ureas from Alloc-, Troc-, and Cbz-carbamates can be a promising approach for the synthesis of useful ureas.
Palladium-catalyzed synthesis of N-aryl carbamates
Vinogradova, Ekaterina V.,Park, Nathaniel H.,Fors, Brett P.,Buchwald, Stephen L.
, p. 1394 - 1397 (2013/04/24)
An efficient synthesis of aryl carbamates was achieved by introducing alcohols into the reaction of palladium-catalyzed cross-coupling of ArX (X = Cl, OTf) with sodium cyanate. The use of aryl triflates as electrophilic components in this transformation a
N-methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the lossen rearrangement
Yoganathan, Sabesan,Miller, Scott J.
, p. 602 - 605 (2013/04/11)
An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.
Palladium-catalyzed carbonylation of amines: Switchable approaches to carbamates and N,N′-disubstituted ureas
Guan, Zheng-Hui,Lei, Hao,Chen, Ming,Ren, Zhi-Hui,Bai, Yinjuan,Wang, Yao-Yu
supporting information; experimental part, p. 489 - 496 (2012/04/04)
Switchable access to carbamates and ureas has been developed by solvent control palladium-catalyzed carbonylation of aromatic amines under an atmosphere of carbon monoxide. A variety of N-phenylcarbamates and N,N′- diphenylureas was easily synthesized in good to excellent yields from readily available aromatic amines under mild conditions. Copyright
