55455-92-0Relevant articles and documents
Synthesis of formamides containing unsaturated groups by: N -formylation of amines using CO2 with H2
Liu, Hangyu,Mei, Qingqing,Xu, Qingling,Song, Jinliang,Liu, Huizhen,Han, Buxing
, p. 196 - 201 (2017/08/15)
Formamides have wide applications in the industry and have been synthesized using CO2 as a carbon source and H2 as a reducing agent. However, previous systems required a noble catalyst and high temperature to achieve high efficiency, and the substrate scope was mostly limited to saturated amines. The selective N-formylation of amines containing unsaturated groups using CO2 and H2 is challenging because the efficient catalysts for the N-formylation are usually very active for hydrogenation of the unsaturated groups. Herein, we achieved for the first time a selective and efficient N-formylation of amines containing unsaturated groups using CO2 and H2 with a Cu(OAc)2-4-dimethylaminopyridine (DMAP) catalytic system. The substrates were converted to the desired formamides, while the unsaturated groups, such as the carbonyl group, the CC bond, CN bond and the ester group remained. The main reason for the excellent selectivity of the Cu(OAc)2-DMAP catalytic system was that it was very active for the N-formylation reaction, but was not active for the hydrogenation of the unsaturated groups.
Rhodium-Catalyzed Bis-Hydroaminomethylation of Linear Aliphatic Alkenes with Piperazine
Seidensticker, Thomas,Vosberg, Jonas M.,Ostrowski, Karoline A.,Vorholt, Andreas J.
supporting information, p. 610 - 621 (2016/02/27)
An efficient protocol was developed to prepare a series of dialkylpiperazines via Rh-catalyzed bis-hydroaminomethylation of linear aliphatic alkenes with piperazine. The well-known Rh/Biphephos catalytic system was applied, yielding the desired dialkylpiperazines within six tandem catalytic steps, already at low catalyst loadings of 0.1 mol%. For the model alkene 1-octene, good yields and linearities of 80% and 77:23, respectively, were achieved under optimized conditions. Influences on the catalytic system regarding n/iso ratio, possible side reactions and the reaction path are discussed on the basis of yield vs. time plots and parameter optimization. With the developed general protocol, other linear, functionalized and branched substrates were effectively transformed to the corresponding linear N,N-disubstituted piperazines.
Solid-Phase Polyamine Synthesis Using Piperazine and Piperidine Building Blocks
Olsen, Christian A.,Witt, Matthias,Jaroszewski, Jerzy W.,Franzyk, Henrik
, p. 4183 - 4185 (2007/10/03)
(Equation presented) Polyamines containing piperidine and piperazine moieties have been synthesized on solid support using SN2 alkylation of resin-bound secondary amines with 2-nitrobenzenesulfonates (nosylates). The effect of solvent on this a
