39655-59-9Relevant academic research and scientific papers
B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of: In situ -formed enamines
Wu, Rongpei,Gao, Ke
supporting information, p. 4032 - 4036 (2021/05/19)
A highly efficient B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines in the presence of water and pinacolborane was developed. Regioselective β-deuteration of tertiary amines was achieved with high chemo- and regioselectivity. D2O was used as a readily available and cheap source of deuterium. Mechanistic studies indicated that B(C6F5)3 could activate water to promote the protonation and reduction of enamines. This journal is
Enantioselective N-Heterocyclic Carbene Catalyzed Cyclopentene Synthesis via the β-Azolium Ylide
Scott, Lydia,Nakano, Yuji,Zhang, Changhe,Lupton, David W.
supporting information, p. 10299 - 10303 (2018/07/31)
Herein we report the cycloisomerization of electron-poor 1,5-dienes via the β-azolium ylide to give enantioenriched cyclopentenes. The reaction is mediated by a chiral N-heterocyclic carbene (NHC) catalyst, exploits readily available substrates, has good generality (17 examples), and displays excellent enantioselectivity (mostly >94:6). Studies demonstrating the viability of a related dynamic kinetic resolution are reported, as are those with alternate tethers and derivatizations.
Synthesis of Chromone-Containing Allylmorpholines through a Morita–Baylis–Hillman-Type Reaction
Chernov, Nikita M.,Shutov, Roman V.,Barygin, Oleg I.,Dron, Mikhail Y.,Starova, Galina L.,Kuz'mich, Nikolay N.,Yakovlev, Igor P.
supporting information, p. 6304 - 6313 (2018/11/10)
The first example of an unusual addition of chromone-substituted acrylic acid to enamines is described. The process shows high versatility concerning both enamines and chromones. The reaction is catalyzed by tertiary amines and is highly likely of Morita–
Dynamic Covalent Chemistry of Aldehyde Enamines: BiIII- and ScIII-Catalysis of Amine–Enamine Exchange
Zhang, Yang,Xie, Sheng,Yan, Mingdi,Ramstr?m, Olof
, 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.
SmI2(H2O)n Reduction of Electron Rich Enamines by Proton-Coupled Electron Transfer
Kolmar, Scott S.,Mayer, James M.
supporting information, p. 10687 - 10692 (2017/08/15)
Samarium diiodide in the presence of water and THF (SmI2(H2O)n) has in recent years become a versatile and useful reagent, mainly for reducing carbonyl-type substrates. This work reports the reduction of several enamines by SmI2(H2O)n. Mechanistic experiments implicate a concerted proton-coupled electron transfer (PCET) pathway, based on various pieces of evidence against initial outer-sphere electron transfer, proton transfer, or substrate coordination. A thermochemical analysis indicates that the C-H bond formed in the rate-determining step has a bond dissociation free energy (BDFE) of ～32 kcal mol-1. The O-H BDFE of the samarium aquo ion is estimated to be 26 kcal mol-1, which is among the weakest known X-H bonds of stable reagents. Thus, SmI2(H2O)n should be able to form very weak C-H bonds. The reduction of these highly electron rich substrates by SmI2(H2O)n shows that this reagent is a very strong hydrogen atom donor as well as an outer-sphere reductant.
Photoinduced oxyamination of enamines and aldehydes with TEMPO catalyzed by [Ru(bpy)3]2+
Koike, Takashi,Akita, Munetaka
supporting information; experimental part, p. 166 - 167 (2010/02/16)
Tris(bipyridyl)rutheriium(II) ([Ru(bpy)3J2+: TB(II)) catalyzes oxidative coupling of enamines and aldehydes with 2,2,6,6- tetramethylpiperidinyl-l-oxy (TEMPO) under irradiation of visible light to afford α-oxyaminated carbonyl compounds. The vi
PROPENYLIDENIMINIUM CATIONS AND 3-(BENZOTRIAZOL-1-YL)-1-AMINO-1-PROPENES BY THE ELIMINATION OF BENZOTRIAZOLE FROM 1,3-BIS(BENZOTRIAZOL-1-YL)PROPYLAMINES
Katritzky, A. R.,Rachwal, S.
, p. 1653 - 1671 (2007/10/02)
1,3-bis(Benzotriazol-1-yl)-N,N-disubstituted propylamines eliminate one mole of benzotriazole on treatment with sodium hydride to give 3-(benzotriazol-1-yl)-1-propen-1-ylamines.In these enamines, the previously unreactive second benzotriazolyl moiety can then undergo ionization to form (2-propenylidene)iminium cations, as was demonstrated by crossover experiments.The propenylideniminium cation undergoes nucleophilic attack by a Grignard reagent either at the first carbon atom to produce the corresponding C-1 substituted allylamines or at the third carbon atom to give enamines.The orientation depends strongly on the conditions and the basicity of the starting amine.Reaction of 2-propenylidenemorpholinium cation (15) with cyanide anions gives 3-morpholinomethacrylonitrile.
SYNTHESIS AND PROPERTIES OF SOME β-TRIORGANOSILYLENAMINES
Kuno, Suzumitsu,Sato, Yoshiro
, p. 309 - 314 (2007/10/02)
Ten β-triorganosilyl-substituted enamines were synthesized by the silylation of β-lithioenamines.They are thermally stable oils but are easily desilylated with protic compounds to give the parent enamines.
