14482-11-2Relevant articles and documents
Effect of phase transfer chemistry, segmented fluid flow, and sonication on the synthesis of cinnamic esters
Riccaboni, Mauro,La Porta, Elena,Martorana, Andrea,Attanasio, Roberta
, p. 4032 - 4039 (2010)
Wittig reaction under Phase Transfer conditions was performed in a flow reaction system. Different bases, aldehydes, phosphonium salts, and flow reaction parameters were investigated, in absence of a phase transfert catalyst. An improvement of the reaction outcome (yield and reaction time) was achieved through the immersion of the reactor into an ultrasound bath.
-
Lorz et al.
, p. 483 (1951)
-
Wittig reaction using perfluorinated ylides
Galante, Aurélie,Lhoste, Paul,Sinou, Denis
, p. 5425 - 5427 (2001)
Wittig reactions could be performed in perfluorosolvents using perfluorinated ylides, allowing both a very easy separation of the alkene from the phosphine oxide and a re-use of the latter by simple reduction of the crude oxide.
C-H activation reactions of ruthenium N-heterocyclic carbene complexes: Application in a catalytic tandem reaction involving C-C bond formation from alcohols
Burling, Suzanne,Paine, Belinda M.,Nama, Devendrababu,Brown, Victoria S.,Mahon, Mary F.,Prior, Timothy J.,Pregosin, Paul S.,Whittlesey, Michael K.,Williams, Jonathan M. J.
, p. 1987 - 1995 (2007)
A series of ruthenium hydride N-alkyl heterocyclic carbene complexes has been investigated as catalysts for a tandem oxidation/Wittig/reduction reaction to give C-C bonds from alcohols. The C-H-activated carbene complex Ru(I iPr2Me2)′(PPh3) 2(CO)H (9) proves to be the most active precursor catalyzing the reaction of PhCH2OH and Ph3P=CHCN in 3 h at 70 °C. These results provide (a) a rare case in which N-alkyl carbenes afford higher catalytic activity than their N-aryl counterparts and (b) a novel example of the importance of NHC C-H activation in a catalytic cycle.
Synthesis of a new Pd(0)-complex supported on boehmite nanoparticles and study of its catalytic activity for Suzuki and Heck reactions in H2O or PEG
Ghorbani-Choghamarani, Arash,Tahmasbi, Bahman,Moradi, Parisa
, p. 43205 - 43216 (2016)
Boehmite nanoparticles are a cubic orthorhombic structure of aluminum oxide hydroxide containing hydroxyl groups attached to their surface, which were prepared in water using commercially available materials. A moisture- and air-stable palladium S-methylisothiourea complex supported on boehmite nanoparticles (Pd(0)-SMTU-boehmite) was prepared using a very simple and inexpensive procedure without an inert atmosphere using commercially available materials. This nanostructure compound was used as an excellent organometallic catalyst for Suzuki and Heck reactions in H2O or PEG-400. The synthesized nanoparticles were characterized using FT-IR, XRD, BET, TGA, TEM, SEM, EDS and ICP-OES techniques. Nitrogen adsorption/desorption measurements indicated that the boehmite nanoparticles have a BET surface area of about 122.8 m2 g-1. This heterogeneous nanocatalyst was easily separated from the reaction mixture and reused for several consecutive runs without significant loss of its catalytic efficiency or palladium leaching. The leaching of palladium from the catalyst was examined using hot filtration and ICP-OES techniques.
4,5-dihydroisoxazoles from arylcyclopropanes: II. Reaction of arylcyclopropanes with nitrosyl chloride activated by sulfur(VI) oxide
Bondarenko,Gavrilova,Kazantseva,Tikhanushkina,Nifant'ev,Saginova,Zyk
, p. 564 - 570 (2007)
Arylcyclopropanes react with nitrosyl chloride activated by sulfur(VI) oxide to give the corresponding 5-aryl-4,5-dihydro-1,2-oxazoles in quantitative yields. The complex NOC1?2SO3 is a highly efficient nitrosating agent which makes it possible to involve in the process arylcyclopropanes having both donor and acceptor substituents in the aromatic ring. Nauka/Interperiodica 2007.
Pd(II)-Catalyzed CC Bond Cleavage by a Formal Group-Exchange Reaction
Ye, Runyou,Zhu, Maoshuai,Yan, Xufei,Long, Yang,Xia, Ying,Zhou, Xiangge
, p. 8678 - 8683 (2021/07/26)
A chelation-assisted palladium-catalyzed CC bond cleavage of α, β-unsaturated ketone to form alkenyl nitrile in the presence of nitrile is disclosed on the basis of a formal group-exchange reaction formulated as C1C2 + C3 → C1C3 + C2, differing from normal alkene oxidative cleavage and metathesis type. The isolated key active Pd(II) complex as well as deuterium-labeled experiment revealed the necessity of the chelation group, and a plausible catalytic pathway was proposed.
Reactions of 3-arylpropenenitriles with arenes under superelectrophilic activation conditions: Hydroarylation of the carbon-carbon double bond followed by cyclization into 3-arylindanones
Gorbunova, Yelizaveta,Zakusilo, Dmitriy N.,Boyarskaya, Irina A.,Vasilyev, Aleksander V.
, (2020/05/25)
Reactions of 3-arylpropenenitriles [ArCH[dbnd]CHCN] with arenes [Ar'H] under the superelectrophilic activation conditions with Br?nsted superacid TfOH (CF3SO3H) or strong Lewis acid AlBr3 result, first, in the formation of products of hydroarylation of the carbon-carbon double bond, 3,3-diarylpropanenitriles [Ar(Ar’)CHCH2CN]. Reactions may go further in TfOH leading to 3-arylindanones, as products of intramolecular aromatic acylation by the electrophilically activated nitrile group. Intermediate cationic species, derived at the protonation of the starting 3-arylpropenenitriles onto the carbon of C[dbnd]C bond and the nitrile nitrogen, have been studied by DFT calculation. A plausible reaction mechanism including the formation of highly reactive dications [(Ar)HC+–CH2C+ = NH] has been proposed. The obtained 3,3-diarylpropanenitriles have been transformed into pharmaceutically valuable 5-(2,2-diarylethyl)-1H-tetrazoles [Ar(Ar’)CHCH2Tetr] and 3-diarylpropylamines [Ar(Ar’)CH(CH2)2NH2] by the reactions with NaN3 and LiAlH4 correspondingly.
