779-54-4Relevant articles and documents
Isotope effects and the nature of stereo- and regioselectivity in hydroaminations of vinylarenes catalyzed by palladium(II)-diphosphine complexes
Vo, Loan K.,Singleton, Daniel A.
, p. 2469 - 2472 (2004)
(Equation Presented) The hydroamination of styrene with aniline catalyzed by phosphine-ligated palladium triflates exhibits a substantial 13C isotope effect at the benzylic carbon. This supports rate-determining nucleophilic attack of amine on a η3-phenethyl palladium complex. Deuterium exchange observations and predicted isotope effects based on DFT calculations support this mechanism. Selectivity in these reactions is determined by the facility of palladium displacement after reversible hydropalladation of the alkene.
Measurements of Heavy-Atom Isotope Effects Using 1H NMR Spectroscopy
Pabis, Anna,Kaminski, Rafal,Ciepielowski, Grzegorz,Jankowski, Stefan,Paneth, Piotr
, p. 8033 - 8035 (2011)
A novel method for measuring heavy-atom KIEs for magnetically active isotopes using 1H NMR is presented. It takes advantage of the resonance split of the protons coupled with the heavy atom in the 1H spectrum. The method is validated by the example of the 13C-KIE on the hydroamination of styrene with aniline, catalyzed by phosphine-ligated palladium triflates.
Cyclometalation of (2 R,5 R)-2,5-diphenylpyrrolidine and 2-phenyl-2-imidazoline ligands with half-sandwich iridium(III) and rhodium(III) complexes
Feghali, Elias,Barloy, Laurent,Issenhuth, Jean-Thomas,Karmazin-Brelot, Lydia,Bailly, Corinne,Pfeffer, Michel
, p. 6186 - 6194 (2013)
Cyclometalation of (2R,5R)-2,5-diphenylpyrrolidine (1) with [(η5-Cp)MCl2]2 using NaOAc in CH 2Cl2 at room temperature, followed by cationization with KPF6 in CH3CN, cleanly yield
Highly enantioselective transfer hydrogenation catalyzed by diasteromeric mixtures of axially chiral (aR,S)- and (aS,S)-Biscarbolines
Dong, Mengxian,Gao, Xinyue,Xiang, Ying,Li, Longfei,Li, Shengnan,Wang, Xuxin,Li, Zhenqiu,Zhu, Huajie
supporting information, (2021/02/05)
The mixtures of axially chiral (aR,S)- and (aS,S)-biscarboline alcohols were firstly used as catalysts in enantioselective 1,2- and 1,4-transfer hydrogenations of ketimines and β-enamino esters, respectively. This mixed axially chiral catalysts exhibited
Chiral Arylated Amines via C?N Coupling of Chiral Amines with Aryl Bromides Promoted by Light
Cao, Rui,Li, Jing-Sheng,Song, Geyang,Tang, Wei-Jun,Wang, Chao,Xiao, Jianliang,Xue, Dong,Yang, Liu,Zhang, Wei
supporting information, p. 21536 - 21542 (2021/08/23)
The Buchwald-Hartwig C-N coupling reaction has found widespread applications in organic synthesis. Over the past two decades or so, many improved catalysts have been introduced, allowing various amines and aryl electrophiles to be readily used nowadays. However, there lacks a protocol that could be used to couple a wide range of chiral amines and aryl halides, without erosion of the enantiomeric excess (ee). Reported in this article is a method based on molecular Ni catalysis driven by light, which enables stereoretentive C-N coupling of optically active amines, amino alcohols, and amino acid esters with aryl bromides, with no need for any external photosensitizer. The method is effective for a wide variety of coupling partners, including those bearing functional groups sensitive to bases and nucleophiles, thus providing a viable alternative to accessing synthetically important chiral N-aryl amines, amino alcohols, and amino acids esters. Its viability is demonstrated by 92 examples with up to 99 % ee.
