51609-04-2Relevant academic research and scientific papers
Selective Palladium(II)-Catalyzed Carbonylation of Methylene β-C?H Bonds in Aliphatic Amines
Cabrera-Pardo, Jaime R.,Trowbridge, Aaron,Nappi, Manuel,Ozaki, Kyohei,Gaunt, Matthew J.
supporting information, p. 11958 - 11962 (2017/09/20)
Palladium(II)-catalyzed C?H carbonylation reactions of methylene C?H bonds in secondary aliphatic amines lead to the formation of trans-disubstituted β-lactams in excellent yields and selectivities. The generality of the C?H carbonylation process is aided by the action of xantphos-based ligands and is important in securing good yields for the β-lactam products.
Reductive amination agents: comparison of Na(CN)BH3 and Si-CBH
Grenga, Paolo N.,Sumbler, Brittany L.,Beland, Fran?ois,Priefer, Ronny
scheme or table, p. 6658 - 6660 (2010/03/03)
Reductive amination is a chemical reaction commonly employed by organic chemists in academics and the pharmaceutical industry. In this reaction a carbonyl group is converted to an amine via an imine intermediate, the formation of which is rate limiting. A major reagent necessary for the completion of this reaction is a hydride source, commonly sodium cyanoborohydride (Na(CN)BH3). The objective of this research was to compare the efficacy of Na(CN)BH3 with silica-bound cyanoborohydride (Si-CBH) as hydride sources in reductive amination reactions. Work has shown that reactions employing Si-CBH as a hydride source showed significant improvement, exhibiting an average percent conversion 25% greater than reactions using Na(CN)BH3.
Reductions of C=O and C=N groups with the systems composed of (η5-C5H5)2MoH2 and acids
Minato, Makoto,Fujiwara, Yutaka,Koga, Miho,Matsumoto, Naoya,Kurishima, Susumu,Natori, Makoto,Sekizuka, Norihiro,Yoshioka, Ken-Ichiro,Ito, Takashi
, p. 139 - 145 (2007/10/03)
Selective reductions of organic compounds, such as carbonyl compounds and imines, using a system composed of Cp2MoH2 and acids are examined. This system can reduce the substrates under mild conditions. Extremely high diastereoselectivity was achieved in the reduction of 4-t-butylcyclohexanone. The reactivity of imines depends on their structure. Aromatic imines are found to be more reactive than aliphatic imines.
Reduction of Schiff Bases with Isopropyl Alcohol and Aluminum Isopropoxide in the Presence of Raney Nickel
Botta, Maurizio,Angelis, Francesco De,Gambacorta, Augusto,Labbiento, Lucia,Nicoletti, Rosario
, p. 1916 - 1919 (2007/10/02)
The reduction of several N-alkyl and N-aryl ketimines to the corresponding secondary amines is described.The reaction, which generally proceeds in high yield, is effected by isopropyl alcohol and aluminium isopropoxide in the presence of Raney nickel.In the absence of the nickel catalyst, that is, under the Meerwein-Ponndorf-Verley conditions, the reaction takes a different route and N-isopropylamines are formed at preference to the direct reduction products.Without the aluminum alkoxide the reduction proceeds only for a small percentage.This reaction, besides offering a new method for the synthesis of secondary amines, represents the first example where the couple aluminum alkoxide/Raney nicel is used in catalytic transfer hydrogenation reactions.
