110480-97-2Relevant academic research and scientific papers
The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst
B?umler, Christoph,Bauer, Christof,Kempe, Rhett
, p. 3110 - 3114 (2020)
The reductive amination of ketones and aldehydes by ammonia is a highly attractive method for the synthesis of primary amines. The use of catalysts, especially reusable catalysts, based on earth-abundant metals is similarly appealing. Here, the iron-catalyzed synthesis of primary amines through reductive amination was realized. A broad scope and a very good tolerance of functional groups were observed. Ketones, including purely aliphatic ones, aryl–alkyl, dialkyl, and heterocyclic, as well as aldehydes could be converted smoothly into their corresponding primary amines. In addition, the amination of pharmaceuticals, bioactive compounds, and natural products was demonstrated. Many functional groups, such as hydroxy, methoxy, dioxol, sulfonyl, and boronate ester substituents, were tolerated. The catalyst is easy to handle, selective, and reusable and ammonia dissolved in water could be employed as the nitrogen source. The key is the use of a specific Fe complex for the catalyst synthesis and an N-doped SiC material as catalyst support.
MOF-derived cobalt nanoparticles catalyze a general synthesis of amines
Jagadeesh, Rajenahally V.,Murugesan, Kathiravan,Alshammari, Ahmad S.,Neumann, Helfried,Pohl, Marga-Martina,Radnik, J?rg,Beller, Matthias
, p. 326 - 332 (2017/09/28)
The development of base metal catalysts for the synthesis of pharmaceutically relevant compounds remains an important goal of chemical research. Here, we report that cobalt nanoparticles encapsulated by a graphitic shell are broadly effective reductive amination catalysts. Their convenient and practical preparation entailed template assembly of cobaltdiamine- dicarboxylic acid metal organic frameworks on carbon and subsequent pyrolysis under inert atmosphere.The resulting stable and reusable catalysts were active for synthesis of primary, secondary, tertiary, and N-methylamines (more than 140 examples).The reaction couples easily accessible carbonyl compounds (aldehydes and ketones) with ammonia, amines, or nitro compounds, and molecular hydrogen under industrially viable and scalable conditions, offering cost-effective access to numerous amines, amino acid derivatives, and more complex drug targets.
Zirconocene Complexes of Imines: General Synthesis, Structure, Reactivity, and in Situ Generation To Prepare Geometrically Pure Allylic Amines
Buchwald, Stephen L.,Watson, Brett T.,Wannamaker, M. Woods,Dewan, John C.
, p. 4486 - 4494 (2007/10/02)
A general method for the preparation of zirconocene complexes of imines has been developed.The X-ray crystal structure of the (trimethylsilyl)benzaldimine complex 2b shows that these complexes should be viewed as metallaaziridenes due to significant ?-donation from the zirconium center to the ?* orbitals of the coordinated imine.These complexes undergo a number of chemo-, regio-, and diastereoselective coupling reactions with unsaturated organic compounds to cleanly form metallacyclic compounds.In situ generation of the complexes followed by coupling with alkynes and hydrolysis affords a general route to geometrically pure allylic amines.
