147410-10-4Relevant academic research and scientific papers
Rhodium catalysts with cofactor mimics for the biomimetic reduction of CN bonds
Chen, Fushan,Deng, Li,Dong, Wenjin,Tang, Jie,Xian, Mo
, p. 5564 - 5569 (2021/08/25)
A strategy based on the cooperation between metal and bonded cofactor mimics was applied to the transfer hydrogenation of CN bonds. We designed and synthesized a rhodium complex containing a 1,3-dimethylbenzoimidazole moiety, which could transfer hydride from a rhodium center to imine substrates in a biomimetic way. Under both transfer hydrogenation and reductive amination reaction conditions, the catalyst exhibited good selectivity towards CN bonds. With the catalyst, 34 imines were transfer hydrogenated to corresponding amines and a key intermediate of retigabine was prepared via reductive amination in a greener way. According to the NMR observations and isotope experiments, a plausible mechanism for this biomimetic reduction of CN bonds were proposed.
Bio-inspired transition metal-organic hydride conjugates for catalysis of transfer hydrogenation: Experiment and theory
McSkimming, Alex,Chan, Bun,Bhadbhade, Mohan M.,Ball, Graham E.,Colbran, Stephen B.
, p. 2821 - 2834 (2015/02/05)
Taking inspiration from yeast alcohol dehydrogenase (yADH), a benzimidazolium (BI+) organic hydride-acceptor domain has been coupled with a 1,10-phenanthroline (phen) metal-binding domain to afford a novel multifunctional ligand (LBI+/sup
Indium-catalyzed hydroamination/hydrosilylation of terminal alkynes and aromatic amines through a one-pot, two-step protocol
Sakai, Norio,Takahashi, Nobuaki,Ogiwara, Yohei
supporting information, p. 5078 - 5082 (2014/08/18)
We demonstrated that indium tribromide effectively functioned as a single catalyst for two successive steps in a one-pot procedure. First, the hydroamination of alkynes with anilines took place to give the Markovnikov product. Then, hydrosilylation of the imine intermediates by treatment with a hydrosilane substrate afforded the corresponding secondary amines.
Bio-inspired catalytic imine reduction by rhodium complexes with tethered hantzsch pyridinium groups: Evidence for direct hydride transfer from dihydropyridine to metal-activated substrate
McSkimming, Alex,Bhadbhade, Mohan M.,Colbran, Stephen B.
, p. 3411 - 3416 (2013/05/08)
Inspired by Nature: A conceptually new design for a catalyst, combining a metal center abutted to an organic hydride donor, is demonstrated for the formate-driven transfer hydrogenation of imines under ambient conditions. A key step, transfer of hydride from the organohydride donor to the metal-polarized substrate, mirrors that in metallo-(de)hydrogenase enzymes.
Cyclopentadienyl N-heterocyclic carbene-nickel complexes as efficient pre-catalysts for the hydrosilylation of imines
Bheeter, Linus P.,Henrion, Mickael,Chetcuti, Michael J.,Darcel, Christophe,Ritleng, Vincent,Sortais, Jean-Baptiste
, p. 3111 - 3116 (2013/12/04)
The in situ generated nickel hydride complex, [Ni(Mes2NHC)HCp], and its cationic analogue, [Ni(Mes2NHC)(NCMe)Cp](PF6), are efficient and chemoselective pre-catalysts for the hydrosilylation of both aldimines and ketimines under mild conditions. The Royal Society of Chemistry.
Nucleophilic Substitution Reaction of 1-Phenylethyl Chlorides in Methanol
Lee, Ikchoon,Lee, Won Heui,Lee, Hai Whang,Bentley, T. W.
, p. 141 - 146 (2007/10/02)
Nucleophilic substitution reactions of 1-(Y-phenyl)ethyl chlorides with X-anilines have been investigated in methanol at 65.0 deg C.An isokinetic point is obtained at ?Y+ = ca. -0.23 with ρX = 0; the sign of ρX changes at this point from positive for the relatively strong electron donating Y substituents to negative for the more electron withdrawing Y substituents. The magnitude of the cross-interaction constant, ρXY, between the substituents X and Y is unusually large with the relatively small magnitude of ρXo resulting in an observable isokinetic point at .These results are interpreted in terms of a transition state (TS) structure in which nearly complete bond formation between the nucleophile and cation formed in an ion-pair preequilibrium is coupled with a TS imbalance phenomenon.The results of kinetic isotope effect studies involving deuteriated anilines and methanol are also in line with this mechanism.
Nucleophilic Substitiution Reactions of 1-Phenylethyl Benzenesulfonates with Anilines in Methanol-Acetonitrile
Lee, Ikchoon,Kim, Hyung Yoon,Kang, Han Keun,Lee, Hai Whang
, p. 2678 - 2683 (2007/10/02)
Nucleophilic substitution reactions of 1-phenylethyl benzenesulfonates with anilines have been investigated in methanol-acetonitrile mixtures at 25 deg C.Magnitudes of the Hammett coefficients ρX, ρY, and ρZ indicate that
