51180-63-3Relevant academic research and scientific papers
Iron-Catalysed Reductive Amination of Carbonyl Derivatives with Ω-Amino Fatty Acids to Access Cyclic Amines
Wei, Duo,Netkaew, Chakkrit,Carré, Victor,Darcel, Christophe
, p. 3008 - 3012 (2019/05/15)
An efficient method for the reductive amination of carbonyl derivatives with ω-amino fatty acids catalysed by an iron complex Fe(CO)4(IMes) [IMes=1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] by means of hydrosilylation was developed. A variety of pyrrolidines, piperidines and azepanes were selectively synthesised in moderate-to-excellent yields (36 examples, 47–97 % isolated yield) with a good functional group tolerance.
Hydrosilylative Reduction of Tertiary Amides to Amines Catalyzed by N-(Phosphinoaryl)anilido Complexes of Iron and Cobalt
Hale, Dylan J.,Murphy, Luke J.,McDonald, Robert,Ferguson, Michael J.,Turculet, Laura
, p. 3818 - 3827 (2019/06/17)
The synthesis and structural characterization of low-coordinate Fe(II) and Co(II) complexes supported by the monoanionic P,N-ligand N-(2-dicyclohexylphosphinophenyl)-2,6-diisopropylanilide are described. A three-coordinate (P,N)Fe-hexamethyldisilazide complex (2), and four-coordinate (P,N)Fe- (3-Fe) and (P,N)Co-alkyl (3-Co) complexes were evaluated as pre-catalysts for the hydrosilylative reduction of amides with PhSiH3 (5 mol % pre-catalyst, 1 equiv. PhSiH3, 80 °C, 1–24 h). The Fe complex 2 proved to be more broadly effective for the reduction of a variety of tertiary amide substrates, and was shown to mediate the reduction of N,N-dibenzylbenzamide at a loading of 1 mol %, to achieve near quantitative formation of tribenzylamine in 1 h (80 °C). Complex 2 also proved effective for the hydrosilylation of tertiary amides under ambient conditions (5 mol % Fe, 24 h), which is a unique example of room temperature amide hydrosilylation mediated by an Fe catalyst without the need for photochemical activation. Given the widespread use of amide reduction protocols in synthesis, the development of efficient Fe-based catalysts that operate under mild conditions is an important target.
A Manganese Pre-Catalyst: Mild Reduction of Amides, Ketones, Aldehydes, and Esters
Kelly, Colin M.,McDonald, Robert,Sydora, Orson L.,Stradiotto, Mark,Turculet, Laura
, p. 15901 - 15904 (2017/12/13)
A new (N-phosphinoamidinate)manganese complex is shown to be a useful pre-catalyst for the hydrosilative reduction of carbonyl compounds, and in most cases at room temperature. The Mn-catalyzed reduction of tertiary amides to tertiary amines, with a useful scope, is demonstrated for the first time by use of this catalyst, and is competitive with the most effective transition-metal catalysts known for such transformations. Ketones, aldehydes, and esters were also successfully reduced under mild conditions by using this new Mn catalyst.
Highly efficient and eco-friendly synthesis of tertiary amines by reductive alkylation of aldehydes with secondary amines over a Pt nanowires catalyst
Wu, Junjie,Lu, Shuanglong,Ge, Danhua,Gu, Hongwei
, p. 81395 - 81398 (2015/10/06)
Plentiful tertiary amine derivates are synthesized by direct formation of tertiary amines by the interaction of aldehydes with secondary amines over Pt nanowires under mild conditions. This method offers a green and rapid approach to transform secondary amines into various tertiary amines.
Palladium(ii)-catalysed ortho-arylation of N-benzylpiperidines
Tan, Peng Wen,Haughey, Maxwell,Dixon, Darren J.
supporting information, p. 4406 - 4409 (2015/03/18)
PdII-catalysed ortho-arylation of benzylic heterocycles with arylboronic acid pinacol esters (Ar-BPin) via directed C-H bond activation to generate the desired biaryl products is reported. This methodology is efficient and applicable to a wide range of functionalised Ar-BPin and benzylic heterocycles, allowing the direct synthesis of important biaryl motifs in modest to good yield. This journal is
Interfacial hydrogenation and deamination of nitriles to selectively synthesize tertiary amines
Lu, Shuanglong,Li, Chao,Wang, Jiaqing,Pan, Yue,Cao, Xueqing,Gu, Hongwei
supporting information, p. 11110 - 11113 (2014/10/15)
A novel one-pot method has been developed for the interfacial hydrogenation of nitriles to synthesize asymmetrical tertiary amines. The active Pt NWs allow for the preparation of a series of tertiary amines in excellent yields (up to 99.0%) and a mixed solvent is vital for the adjustment of the yield. And also, the reaction proceeded under mild conditions and is environmentally friendly.
Reinvestigation of aminomethyltrifluoroborates and their application in suzuki-miyaura cross-coupling reactions
Raushel, Jessica,Sandrock, Deidre L.,Josyula, Kanth V.,Pakyz, Deborah,Molander, Gary A.
experimental part, p. 2762 - 2769 (2011/06/17)
A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.
Scope of aminomethylations via Suzuki-Miyaura cross-coupling of orsanotrifluoroborates
Molander, Gary A.,Gormisky, Paul E.,Sandrock, Deidre L.
, p. 2052 - 2057 (2008/09/19)
(Chemical Equation Presented) We previously reported the Suzuki-Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to excellent yields to give N,N-dialkylbenzylic amines. The aminomethylation of alkenyl bromides was also examined.
Method for producing amines by homogeneously catalyzed reductive amination of carbonyl compounds
-
Page/Page column 12; 17-18, (2010/02/11)
The invention relates to the preparation of chiral or achiral amines by reaction of aldehydes or ketones with ammonia or primary or secondary amines in the presence of hydrogen and in the presence of homogeneous metal catalysts under mild conditions. Metal catalysts which can be used are complexes of late transition metals with chiral or achiral phosphorus-containing ligands.
On the reductive amination of aldehydes and ketones catalyzed by homogeneous Rh(I) complexes
Tararov,Kadyrov,Riermeier,Borner
, p. 1867 - 1868 (2007/10/03)
The homogeneously catalyzed reductive amination of aldehydes and ketones under smooth conditions is reported, showing for the first time, that Rh(I) catalysts based on chelating diphosphines and diphosphinites can be advantageously employed for this reaction, even for the production of chiral amino acid derivatives.
