83871-63-0Relevant academic research and scientific papers
Samarium Diiodide-Promoted Reductive Coupling of Imines
Imamoto, Tsuneo,Nishimura, Seijiro
, p. 1141 - 1142 (1990)
Aromatic aldimines are reductively coupled to 1,2-diamines by treatment with samarium diiodide.Cross-coupling of aromatic ketimines with ketones to 2-aminoalcohols is also promoted by the same reagent.
Synergistic Photoredox Catalysis and Organocatalysis for Inverse Hydroboration of Imines
Zhou, Nengneng,Yuan, Xiang-Ai,Zhao, Yue,Xie, Jin,Zhu, Chengjian
, p. 3990 - 3994 (2018/03/21)
The first catalytic inverse hydroboration of imines with N-heterocyclic carbene (NHC) boranes has been realized by means of cooperative organocatalysis and photocatalysis. This catalytic combination provides a promising platform for promoting NHC-boryl radical chemistry under sustainable and radical-initiator-free conditions. The highly important functional-group compatibility and possible application in late-stage hydroborations represent an important step forward to an enhanced α-amino organoboron library.
Salt/ligand-activated low-valent titanium formulations: the 'salt effect' on diastereoselective carbon-carbon bond forming SET reactions
Rele, Shyam M.,Nayak, Sandip K.,Chattopadhyay, Subrata
, p. 7225 - 7233 (2008/12/20)
A comprehensive study on the influence of exogenously added electropositive metal salts as promoters/secondary activators on preformed LVT species has resulted in the construction of highly efficient low-valent titanium (LVT) reagents. These salt-activated LVT reagents while exhibiting enhanced chemoselectivity and diastereoselectivity accelerated the reductive olefination rates of aromatic and aliphatic carbonyls under ambient temperature conditions and in much reduced reaction times. The versatility of the salted reagent was further explored in other single electron transfer reactions, namely, imino-pinacol couplings and one-pot synthesis of phenanthrenes from o-alkoxy aromatic carbonyls. We envisage that, in contrast to multiphase heterogeneous colloidal slurries, salt-activated LVT reagents afforded uniformly viscous homogeneous slurries generating a highly reactive monomeric intermetallic LVT complex. Continued judicious exploration of the emerging paradigms by studying the influence of external ligands/auxiliaries/redox agents on LVT reagents, and organometallics in general, will be critical to widen the scope and utility of the classical McMurry reaction and other SET reactions.
Reductive dimerization and reduction of imines using lanthanum metal
Nishino, Toshiki,Nishiyama, Yutaka,Sonoda, Noboru
, p. 131 - 135 (2007/10/03)
The treatment of N-benzylideneaniline (1a) with a half-equivalent of lanthanum metal and a catalytic amount of iodine gave the reductive dimerization product of 1a, a vic-diamine, in good yield. Various vic-diamines were synthesized from aldimines in this
Indium-mediated deoxygenation of nitrones, N-oxides and deoxygenative reductive coupling of nitrones to vicinal diamines
Jeevanandam, Arumugasamy,Cartwright, Charles,Ling, Yong-Chien
, p. 3153 - 3160 (2007/10/03)
We reported transformation of nitrones selectively either to aldamines or vicinal diamines and deoxygenation of N-oxides using Indium at ambient temperature in good yields.
Organic reaction in water. Part 1. A convenient method for reduction of imines using zinc powder
Tsukinoki, Takehito,Mitoma, Yoshiharu,Nagashima, Satoko,Kawaji, Takatoshi,Hashimoto, Iwao,Tashiro, Masashi
, p. 8873 - 8876 (2007/10/03)
Reduction of imines was performed with zinc powder in 5% aqNaOH solution without any organic solvents under mild conditions, and the corresponding amines were obtained in good yields.
Reductive coupling of aldimines mediated with samarium catalyzed by Cp2TiCl2
Liao, Puhong,Huang, You,Zhang, Yongmin
, p. 1483 - 1486 (2007/10/03)
Reductive coupling of aldimines into vicinal diamines mediated with samarium catalyzed by Cp2TiCl2 proceeds in refluxing THF with good yields.
Electrosynthesis of N-Substituted DL-Arylglycineesters and 1,2-Diarylamino-1,2-diarylethanes by Cathodic Reduction of Azomethines in the Presence of Carbon Dioxide
Hess, U.,Thiele, R.
, p. 385 - 399 (2007/10/02)
The electroreduction of the N-arylidene-arylamines 1-12 in CO2-saturated solvents of low proton availability as DMF at markedly more positive potentials than carbon dioxide end up in carboxylating the C-atom and hydrogenating the nitrogen of the C=N-double bond.The resulting N-arylsubstituted DL-arylglycines and traces of carbamates may be isolated as esters, adding ethylchloride during the electrolysis.A competing pathway of the electrocarboxylation is the C-C-hydrodimerisation and the hydrogenation of the C=N-double bond, whose importance increases with the water content of the solvent.Based on cyclic-voltametric evidence and product analysis the mechanism of the reductive electrocarboxylation reaction is discussed in terms of nucleophilic attack of the azomethine anion radical on a proton or CO2.
