39166-25-1Relevant articles and documents
Hydrogen-Bond-Promoted Metal-Free Hydroamination of Alkynes
Bahri, Janet,Monnier, Florian,Ollevier, Thierry,Taillefer, Marc,Tanbouza, Nour
supporting information, p. 2086 - 2090 (2019/11/05)
An original metal-free regio- A nd stereoselective intermolecular hydroamination of alkynes is described. Various (E)-enamines were obtained from arylacetylenes and aliphatic secondary amines in the presence of ethylene glycol as a solvent. The latter is
Regio- and Enantioselective Formal Hydroamination of Enamines for the Synthesis of 1,2-Diamines
Yu, Lu,Somfai, Peter
supporting information, p. 8551 - 8555 (2019/05/21)
The asymmetric formal hydroamination of enamines using a CuH catalyst is reported. The method provides a straightforward and efficient approach to the synthesis of chiral 1,2-dialkyl amines in good yields with high levels of enantioselectivities for a broad range of substrates, and should have significant value for the preparation of molecules bearing a 1,2-diamine motif.
The pyrrole ring η2-hapticity bridged binuclear tricarbonyl Mo(0) and W(0) complexes: catalysis of regioselective hydroamination reactions and DFT calculations
Jha, Vikesh Kumar,Mani, Ganesan,Davuluri, Yogeswara Rao,Anoop, Anakuthil
supporting information, p. 1840 - 1847 (2017/02/23)
Following the report of the ferrocene structure, metal complexes containing the heteroatom-substituted cyclopentadienyl (Cp) analogue, that is the η5 pyrrolyl ligand, have been reported. While the Cp ligand continues to be a favorite ligand in
Dynamic Covalent Chemistry of Aldehyde Enamines: BiIII- and ScIII-Catalysis of Amine–Enamine Exchange
Zhang, Yang,Xie, Sheng,Yan, Mingdi,Ramstr?m, Olof
supporting information, p. 11908 - 11912 (2017/09/07)
The dynamic exchange of enamines from secondary amines and enolizable aldehydes has been demonstrated in organic solvents. The enamine exchange with amines was efficiently catalyzed by Bi(OTf)3 and Sc(OTf)3 (2 mol %) and the equilibria (60 mm) could be attained within hours at room temperature. The formed dynamic covalent systems displayed high stabilities in basic environment with 2 % by-product formation within one week after complete equilibration. This study expands the scope of dynamic C?N bonds from imine chemistry to enamines, enabling further dynamic methodologies in exploration of this important class of structures in systems chemistry.
An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides
Slagbrand, Tove,Kervefors, Gabriella,Tinnis, Fredrik,Adolfsson, Hans
, p. 1990 - 1995 (2017/06/09)
A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).
Facile preparation of pyrimidinediones and thioacrylamides: Via reductive functionalization of amides
Trillo, Paz,Slagbrand, Tove,Tinnis, Fredrik,Adolfsson, Hans
, p. 9159 - 9162 (2017/08/17)
The development of an efficient protocol for the reductive functionalization of amides into pyrimidinediones and amino-substituted thioacrylamides is presented. Enamines are generated in a highly chemoselective amide hydrosilylation reaction catalyzed by
1,3-Dipolar cycloaddition reactivities of perfluorinated aryl azides with enamines and strained dipolarophiles
Xie, Sheng,Lopez, Steven A.,Ramstr?m, Olof,Yan, Mingdi,Houk
supporting information, p. 2958 - 2966 (2015/03/18)
The reactivities of enamines and predistorted (strained) dipolarophiles toward perfluoroaryl azides (PFAAs) were explored experimentally and computationally. Kinetic analyses indicate that PFAAs undergo (3 + 2) cycloadditions with enamines up to 4 orders of magnitude faster than phenyl azide reacts with these dipolarophiles. DFT calculations were used to identify the origin of this rate acceleration. Orbital interactions between the cycloaddends are larger due to the relatively low-lying LUMO of PFAAs. The triazolines resulting from PFAA-enamine cycloadditions rearrange to amidines at room temperature, while (3 + 2) cycloadditions of enamines and phenyl azide yield stable, isolable triazolines. The 1,3-dipolar cycloadditions of norbornene and DIBAC also show increased reactivity toward PFAAs over phenyl azide but are slower than enamine-azide cycloadditions.
Efficient and selective synthesis of e-vinylamines via tungsten(0)-catalyzed hydroamination of terminal alkynes
Kocicka, Paulina,Czelusniak, Izabela,Szymaska-Buzar, Teresa
supporting information, p. 3319 - 3324 (2015/01/09)
The hydroamination of terminal alkynes (RC≡CH=phenylacetylene, 4-methylphenylacetylene, 4-fluorophenylacetylene, 1-hexyne, methyl 2-propynyl ether, prop-2-yn-1-ol) with secondary amines (piperidine, pyrrolidine, morpholine, piperazine, methylpiperazine, 4
Catalytic reductive dehydration of tertiary amides to enamines under hydrosilylation conditions
Volkov, Alexey,Tinnis, Fredrik,Adolfsson, Hans
supporting information, p. 680 - 683 (2014/03/21)
Tertiary amides are efficiently reduced to their corresponding enamines under hydrosilylation conditions, using a transition-metal-free catalytic protocol based on t-BuOK (5 mol %) and (MeO)3SiH or (EtO) 3SiH as the reducing agent. The enamines were formed with high selectivity in good-to-excellent yields.
Inverse electron demand hetero-Diels-Alder reaction in preparing 1,4-benzodioxin from o-quinone and enamine
Zhang, Jinsong,Taylor, Chris,Bowman, Erich,Savage-Low, Leo,Lodewyk, Michael W.,Hanne, Larry,Wu, Guang
supporting information, p. 6298 - 6302 (2013/11/06)
A process for synthesizing 1,4-benzodioxin, through oxidation of a phenol to an o-quinone followed by treatment with an enamine, has been developed. Adduct stereochemistry is found to be retained via this one-pot reaction. The method uses hypervalent iodine reagent under mild conditions and is compatible with a wide scope of phenols and enamines.