- Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions
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A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepered MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS analysis confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP analysis showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions.
- Niknam, Esmaeil,Panahi, Farhad,Khalafi-Nezhad, Ali
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supporting information
(2021/01/12)
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- NiFe2O4@SiO2@ZrO2/SO42-/Cu/Co nanoparticles: A novel, efficient, magnetically recyclable and bimetallic catalyst for Pd-free Suzuki, Heck and C-N cross-coupling reactions in aqueous media
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The novel heterogeneous bimetallic nanoparticles of Cu-Co were synthesized based on magnetic nanoparticles, and the magnetic nanocatalyst was characterized by XRD, FE-SEM, EDX mapping, BET, TEM, HRTEM, FTIR, TGA, and VSM. This catalyst was successfully applied as a recyclable magnetically catalyst in Heck, Suzuki, and C-N cross-coupling reactions with various aryl halides (iodides, bromides, and chlorides as challengeable substrates), with olefins, phenylboronic acid, and amines, respectively. We considered the rise of synergetic effects from the different Lewis acid and Br?nsted acid sites present in the catalyst. The catalyst was synthesized with cheap, available materials and a simple synthesis method. The catalyst can be separated easily using an external magnet. It was recycled for more than ten runs without a sensible loss of its catalytic activity, and no significant leaching of the Cu and Co quantity was observed. The significant benefits of the method are high-level generality, simple operation, and there are no heavy metals and toxic solvents. This is a quick, easy, efficacious and environmentally friendly protocol, and no by-products are formed in the reaction. These features make it an appropriate practical alternative protocol. In comparison with recent works, the other advantage of this catalyst is the synthesis of a wide variety of C-C and C-N bond derivatives (more than 40 derivatives). The other significant advantage is the low temperature of the reaction and the use of the least possible amount of the catalyst (0.003 g). The efficiency was good to excellent and the catalyst selectivity has been high. We aspire that our study inspires more interest to design novel catalysts based on using low-cost metal ions (such as cobalt and copper) in the cross-coupling reactions. This journal is
- Alavi G., Seyyedeh Ameneh,Nasseri, Mohammad Ali,Kazemnejadi, Milad,Allahresani, Ali,Hussainzadeh, Mahdi
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p. 7741 - 7757
(2021/05/13)
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- Palladium anchored on guanidine-terminated magnetic dendrimer (G3-Gu-Pd): An efficient nano-sized catalyst for phosphorous-free Mizoroki-Heck and copper-free Sonogashira couplings in water
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In this research, a novel type of Fe3O4&at;silica-supported dendrimer capped by guanidine groups for immobilization of palladium was reported. This novel nano-sized catalyst was characterized by FTIR, TGA, XRD, FESEM, EDX, VSM, XPS and HRTEM methods. Enhanced catalytic activity of the prepared catalyst in Mizoroki-Heck and copper-free Sonogashira coupling reactions were evaluated in water as a green solvent. The influence of the various reaction parameters such as catalyst dosage, time and temperature on two mentioned C–C coupling reactions were studied. Results showed that the catalyst could be easily recovered by simple separation by an external magnet and reused for five cycles of recovery without considerable losing of its activity.
- Khalafi-Nezhad, Ali,Moaddeli, Ali,Niknam, Esmaeil
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- First Cp*Co(III)-catalyzed Mizoroki-Heck coupling reactions of alkenes and aryl bromide/iodide
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A Cp*Co(CO)I2 catalyzed Mizoroki-Heck coupling of alkenes and aryl halide is established at feasible reaction conditions. The Cp*Co(III) catalyst excellently work to couple the aryl iodide and alkene, and produce up to 94% yield of the coupling
- Srivastava, Avinash K.,Satrawala, Naveen,Ali, Munsaf,Sharma, Charu,Joshi, Raj K.
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supporting information
(2019/11/13)
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- Diarylethene synthesis method without transition metal catalysis
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The invention discloses a diarylethene synthesis method without transition metal catalysis. The method comprises the following steps: a cinnamic acid derivative and aryl trifluoroborate are subjectedto a decarboxylation coupling reaction in a solvent under the action of an oxidizing agent, postprocessing is performed after the reaction, and diarylethene is obtained. K2S2O8 is adopted to promote acatalytic system in the synthetic method, and a free radical coupling reaction can be performed directly under the condition that no ligand, transition metal or alkali is added. The method has widersubstrate range and higher yield; the method is simple to operate, reaction conditions are mild, and large-scale application is facilitated.
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Paragraph 0046-0050
(2019/02/06)
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- Preparation method of palladium catalyzed 1,2-trans diaryl alkene
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The invention discloses a preparation method of palladium catalyzed 1,2-trans diaryl alkene. The method comprises the following steps that under the effects of catalysts, cocatalysts and alkali, arylacrylic acid and aromatic esters p-toluene sulfonate take decarboxylation coupling reaction in an organic solvent; after the reaction is finished, the 1,2-trans diaryl alkene is obtained through posttreatment. The method has the advantages that through C-O bond fracture, the operation is simple; a stable palladium catalyst with low cost is used; the substrate applicability is high; the harsh reaction conditions and the addition of strong alkali are not needed; the trans 1,2-diaryl alkene can be generated at high selectivity.
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Paragraph 0046-0048
(2019/06/11)
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- Palladium-catalyzed decarboxylative coupling of α,β-unsaturated carboxylic acids with aryl tosylates
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We report a general method for selective cross-coupling of α,β-unsaturated carboxylic acids with aryl tosylates enabled by versatile Pd(II) complexes. This method features the general cross-coupling of ubiquitous α,β-unsaturated carboxylic acids by decarboxylation. The transformation is characterized by its operational simplicity, the use of inexpensive, air-stable Pd(II) catalysts, scalability and wide substrate scope. The reaction proceeds with high trans selectivity to furnish valuable (E)-1,2-diarylethenes.
- Zhang, Wei,Chen, Gairong,Wang, Kaikai,Xia, Ran
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- Phosphanamine-functionalized magnetic nanoparticles (PAFMNP): An efficient magnetic recyclable ligand for the Pd-catalyzed Heck reaction of chloroarenes
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A phosphanamine-functionalized trimethoxysilyl compound (DPPPA) was synthesized and reacted with magnetic nanoparticles in order to synthesise a novel magnetic reusable phosphanamine ligand (PAFMNP) for application in transition metal-catalyzed coupling reactions. The Pd complex of PAFMNP (Pd-PAFMNP) was found to be an efficient heterogeneous catalyst for the Heck reaction of aryl chlorides. Only 1.0 mol% of catalyst was needed to accomplish the Heck reaction of the aryl chlorides. The catalyst was reusable at least 5 times without a significant decrease in its catalytic activity.
- Panahi, Farhad,Zarnaghash, Narges,Khalafi-Nezhad, Ali
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p. 1250 - 1255
(2016/02/19)
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- Synthesis of new surfactant-like triazine-functionalized ligands for Pd-catalyzed Heck and Sonogashira reactions in water
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In this study, a novel class of ligands for palladium-catalyzed C-C coupling reactions in water is introduced. A range of triazine-functionalized ligands were synthesized using 2,4,6-trichloro-1,3,5-triazine (TCT) reagent. Among them, N2,N4,N6-tridodecyl-1,3,5-triazine-2,4,6-triamine (TDTAT) was found to be an efficient ligand for the Pd-catalyzed Heck and Sonogashira reactions in water, which acted as a green solvent. TEM analysis showed that in the presence of TDTAT in water at 80°C, PdCl2 is converted to nanoparticles with an average size of ~3 nm. The formed Pd-nanoparticles act as efficient catalytic species for C-C bond formation reactions in neat water. Under these conditions, Pd-catalyzed Heck and Sonogashira reactions are accomplished without the need for phosphine ligand. The generation of emulsion droplets (5-10 μm) containing Pd(0) nanoparticles would function as an effective reactor to accelerate the rate of the reaction in water media.
- Iranpoor, Nasser,Rahimi, Sajjad,Panahi, Farhad
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p. 49559 - 49567
(2015/06/16)
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- Pd(II) complexes with amide-based macrocycles: Syntheses, properties and applications in cross-coupling reactions
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This work shows Pd(ii) complexes in a set of 13-membered amide-based macrocyclic ligands varied by the placement of e--donating and e--withdrawing substituents on the ligand framework. Ligands constitute a N4 square-planar cavity and optimally house the Pd(ii) ion. The solution-state structure via NMR and absorption spectra substantiates the solid-state structure obtained by crystallography. The electrochemical studies display the impact of electronic substituents on ligands that significantly influence the redox properties and also shift the locus of oxidation. These complexes were used in the Suzuki and Heck cross-coupling reactions. The moderate cross-coupling reaction results are due to limited redox accessibility that can be improved either by using substrates with a better leaving group or by placing electron-withdrawing substituents on the macrocyclic ligands.
- Kumar, Sushil,Jha, Rajeev Ranjan,Yadav, Sunil,Gupta, Rajeev
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p. 2042 - 2051
(2015/03/18)
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- Imidazolium ionic liquid-tagged palladium complex: An efficient catalyst for the Heck and Suzuki reactions in aqueous media
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An air stable, water soluble, and efficient ionic liquid-tagged Schiff base palladium complex was prepared. The synthesized complex was well characterized by NMR, mass spectrometry, FT-IR, UV-visible spectroscopy and powder X-ray diffraction. The complex was used as a catalyst for the Suzuki and Heck cross-coupling reactions in water. Good to excellent yields were achieved using a modest amount of the catalyst. In addition, the catalyst can be easily reused and recycled for six steps without much loss in activity, exhibiting an example of sustainable and green methodology. the Partner Organisations 2014.
- Nehra, Pankaj,Khungar, Bharti,Pericherla, Kasiviswanadharaju,Sivasubramanian,Kumar, Anil
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p. 4266 - 4271
(2014/09/29)
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- Substituent effects on the 13C NMR chemical shifts of the imine carbon in N-(4-X-benzylidene)-4-(4-Y-styryl) anilines
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Long-range electronic substituent effects were targeted using the substituent dependence of δC(C=N), and specific cross-interactions were explored extendedly. A wide set of N-(4-X-benzylidene)- 4-(4-Y-styryl) anilines, p-X-C6H4
- Fang, Zhengjun,Cao, Chenzhong,Chen, Guanfan
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p. 1343 - 1350
(2013/08/24)
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- Mechanically activated synthesis of (E)-stilbene derivatives by high-speed ball milling
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An efficient mechanically activated solvent-free synthesis of (E)-stilbene derivatives by high-speed ball milling is described. This method has notable advantages in terms of good yield, short reaction time and high selectivity. Copyright
- Zhu, Xingyi,Liu, Jun,Chen, Tao,Su, Weike
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experimental part
p. 145 - 147
(2012/05/05)
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- Catalytic application of dinuclear palladium(II) bis(thiosemicarbazone) complex in the Mizoroki-Heck reaction
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A convenient synthesis of new square planar dinuclear palladium(II) terephthaldehyde bis(thiosemicarbazone) complex has been described. The compositions of the complex have been established by elemental analysis, spectral methods and single crystal X-ray crystallographic technique. The new complex acts as an active recyclable homogeneous catalyst for the Mizoroki-Heck reaction of electron deficient (activating) and electron rich (deactivating) aryl halides with various olefins under optimized conditions.
- Prabhu, Rupesh Narayana,Ramesh, Rengan
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supporting information
p. 5961 - 5965,5
(2020/08/20)
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- N-Heterocyclic carbene-Pd(II) complex derived from proline for the Mizoroki-Heck reaction in water
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N-Heterocyclic carbene-Pd(II) complex 1 derived from proline was found to be an efficient catalyst in the Mizoroki-Heck reaction of aryl bromides and iodides performed in water. The reactions can tolerate various functional groups in the substrates and all gave the corresponding coupling products in good to high yields.
- Tang, Yi-Qiang,Chu, Chun-Yan,Zhu, Lei,Qian, Bin,Shao, Li-Xiong
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experimental part
p. 9479 - 9483
(2011/12/15)
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- The synthesis and structure-activity relationship of substituted N-phenyl anthranilic acid analogs as amyloid aggregation inhibitors
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It is believed that β-amyloid aggregation is an important event in the development of Alzheimer's disease. In the course of our studies to identify β-amyloid aggregation inhibitors, a series of N-phenyl anthranilic acid analogs were synthesized and studied for β-amyloid inhibition activity. The synthesis, structure-activity relationship, and in vivo activity of these analogs are discussed.
- Simons, Lloyd J.,Caprathe, Bradley W.,Callahan, Michael,Graham, James M.,Kimura, Takenori,Lai, Yingjie,LeVine III, Harry,Lipinski, William,Sakkab, Annette T.,Tasaki, Yoshikazu,Walker, Lary C.,Yasunaga, Tomoyuki,Ye, Yuyang,Zhuang, Nian,Augelli-Szafran, Corinne E.
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scheme or table
p. 654 - 657
(2009/09/06)
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- Heterogeneous Pd/C-catalyzed ligand-free, room-temperature suzuki-miyaura coupling reactions in aqueous media
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A mild and efficient ligand-free Suzuki-Miyaura coupling reaction catalyzed by heterogeneous Pd/C was developed. Aryl bromides and triflates undergo the cross-coupling with aryl boronic acids in excellent yields without the presence of any additives in aqueous media at room temperature. Aryl vinyl boronic acids are also applicable to this coupling reaction and provide the trans-stilbene derivatives in high yields. The application of wet-type Pd/C to the coupling reaction was achieved without any loss of activity under aerobic conditions, and the reuse of Pd/C is feasible for a fifth run without significant loss of activity. Inductively coupled plasma (ICP) mass-spectrometric analysis of the filtrate from the reaction mixture of 4-bromonitrobenzene with phenylboronic acid demonstrated that the palladium metal hardly leached into the solution within the limits of the detector ( 1 ppm), thus suggesting that the present Suzuki-Miyaura reaction proceeded by heterogeneous catalysis.
- Maegawa, Tomohiro,Kitamura, Yoshiaki,Sako, Satoko,Udzu, Takahiro,Sakurai, Ai,Tanaka, Asami,Kobayashi, Yusuke,Endo, Koichi,Bora, Utpal,Kurita, Takanori,Kozaki, Atsushi,Monguchi, Yasunari,Sajiki, Hironao
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p. 5937 - 5943
(2008/02/13)
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- Aqueous Wittig reactions of aldehydes with in situ formed semistabilized phosphorus ylides
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The Wittig reactions of three semistabilized phosphorus ylides generated in situ from the corresponding phosphonium salts with aldehydes in water without any organic cosolvent were investigated. Most of the olefination reactions completed within between 5 min and 4.5 h in refluxing water containing 1.5 equiv of LiOH and 1.4M LiCl to afford the products in 65-100% yields. The E:Z selectivity depended not only on the substituent attached to the benzene ring of the ylides but also on the substituent bound to the aromatic aldehydes. LiCl promotes the aqueous Wittig reactions and suppresses decomposition of the ylide or the corresponding phosphonium salt. Copyright Taylor & Francis, Inc.
- Wu, Jinlong,Zhang, Da
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p. 2543 - 2551
(2007/10/03)
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- Spectroscopic Correlations between Supermolecules and Molecules. Anatomy of the Ion-Modulated Electronic Properties of the Nitrogen Donor in Monoazacrown-Derived Intrinsic Fluoroionophores
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The synthesis, absorption and emission spectra, fluorescence quantum yields, and fluorescence lifetimes of three compound series of trans-4,4′-disubstituted aminostilbenes (1-3) are reported. The chromo-/fluoroionophoric behavior of the monoaza-15-crown-5
- Yang, Jye-Shane,Hwang, Chung-Yu,Hsieh, Chia-Chun,Chiou, Shih-Yi
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p. 719 - 726
(2007/10/03)
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- N-acylamino benzyl ether derivatives
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This invention relates to N-acylamino aryl derivatives of the formula 1where R1, R21, R22, R23, R3, R4, R5 R6, R7, R8, R, and n are as defined herein and where X is —CHRO, —OCHR—, —CH2S—, —SCH2—, —CH2CH2—, —CH=CH— or —C≡C—. The compounds of the invention are selective monoamine oxidase B inhibitors, and they are therefore useful in the treatment of diseases mediated by monoamine oxidase B, for example, for the treatment of Alzheimer's disease or senile dementia.
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- N-ACYLAMINOBENZENE DERVATIVES AS SELECTIVE MONOAMINE OXIDASE B INHIBITORS
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This invention relates to N-acylamino aryl derivatives of the general formula (I), wherein R1 is halogen, halogen-(C1-C6)-alkyl, cyano, C1-C6-alkoxy or halogen-(C1-C6)-alkoxy; R
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- Platinum-catalyzed cross-couplings of organoboronic acids with aryl iodides
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Tetrakis(triphenylphosphine)platinum in DMF was utilized as a mild catalyst for cross coupling reactions of organoboronic acids with aryl iodides. The present reactions exhibited excellent group-selectivity where couplings of organoboronic acids 2a-e with 4-bromo-1-iodobenzene (4) give 4-arylbromobenzenes 5a-b and 4-alkenylbromobenzenes 5c-e in excellent yields.
- Oh, Chang Ho,Lim, Young Mook,You, Choong Ho
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p. 4645 - 4648
(2007/10/03)
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- Oxime-Derived Palladium Complexes as Very Efficient Catalysts for the Heck-Mizoroki Reaction
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Oxime-derived, chloro-bridged palladacycles 16 are efficient complexes for the Heck vinylation of aryl halides. The isolated catalysts are thermally stable, not sensitive to air or moisture and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions, with aryl iodides, bromides and chlorides with acrylic esters and olefins displaying turnover numbers (TON) of up to 1010 for phenyl iodide and turnover frequencies (TOF) of 1.4 × 108 h-1. Deactivated aryl bromides undergo the Heck reaction with styrene with TON and TOF values up to 97,000 and 6063 h-1, respectively. Even aryl chlorides undergo the coupling reaction with olefins with TON up to 920. Complexes 16 catalyze the synthesis of 2,3-disubstituted indenones and indoles in good yields via annulation reaction of internal alkynes with o-bromoor o-chlorobenzaldehyde and o-iodoaniline, respectively.
- Alonso, Diego A.,Najera, Carmen,Pacheco, Ma. Carmen
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p. 172 - 183
(2007/10/03)
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- Synthesis, structure-activity relationships, and pharmacokinetic properties of dihydroorotate dehydrogenase inhibitors: 2-cyano-3-cyclopropyl- 3-hydroxy. N-[3'-methyl-4'-(trifluoromethyl)phenyl]propenamide and related compounds
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The active metabolite (2) of the novel immunosuppressive agent leflunomide (1) has been shown to inhibit the enzyme dihydroorotate dehydrogenase (DHODH). This enzyme catalyzes the fourth step in de novo pyrimidine biosynthesis. A series of analogues of the active metabolite 2 have been synthesized. Their in vivo biological activity determined in rat and mouse delayed type hypersensitivity has been found to correlate well with their in vitro DHODH potency. The most promising compound (3) has shown activity in rat and mouse collagen (II)-induced arthritis models (ED50 = 2 and 31 mg/kg, respectively) and has shown a shorter half-life in man when compared with leflunomide. Clinical studies in rheumatoid arthritis are in progress.
- Kuo, Elizabeth A.,Hambleton, Philip T.,Kay, David P.,Evans, Phillip L.,Matharu, Saroop S.,Little, Edward,McDowall, Neil,Jones, C. Beth,Hedgecock, Charles J. R.,Yea, Christopher M.,Chan, A. W. Edith,Hairsine, Peter W.,Ager, Ian R.,Tully, W. Roger,Williamson, Richard A.,Westwood, Robert
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p. 4608 - 4621
(2007/10/03)
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- Substituent effects on the genotoxicity of 4-nitrostilbene derivatives
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4-Nitrostilbene and twelve of its derivatives (eleven E-stilbenes and two Z-stilbenes) were examined for possible quantitative structure-activity relationships of their in vitro and in vivo genotoxicity. Relative mutagenicity was studied with and without S9 activation in Salmonella strains TA98 and TA100, as well as in the nitroreductase deficient strains TA98/NR and TA100/NR. Chromosomal aberrations in the bone-marrow cells of mice following intraperitoneal administration of the nitrostilbenes were observed as an indicator of in vivo genotoxicity. All of the compounds were active in TA98 and TA100 without S9 activation, with the exception of 4-amino-4'-nitrostilbene in TA100. Mutagenic activity was greatly reduced or eliminated in the NR strains, which is consistent with metabolic activation of the compounds by bacterial reductase. The presence of S9 lowered the activity of most of the nitrostilbenes presumedly by enzymatic detoxication. Hammet values of substituents, partition coefficients and frontier orbital energies (E(LUMO) and E(HOMO)) were studied for correlations with mutagenicity of the eleven E-stilbenes. Correlations could be established between mutagenicity in TA98 without S9 activation and the Hammet values. The same mutagenicity could also be correlated to E(LUMO). Rationales for these correlations include the concept that electron-withdrawing groups which lower E(LUMO) should facilitate the reduction of the nitro group, leading to the proximate mutagen hydroxylamine. The correlations are also explained by the concept that electron-withdrawing groups should help stabilize the hydroxylamine intermediate and make the ultimate mutagenic species, the nitrenium ions, more reactive toward DNA. The relationship between mutagenicity and electronic effects of substituent groups found in vitro could not be extended to the in vivo results. However, except for the dinitrostilbenes, where insolubility prevented their testing, all the nitrostilbenes produced a statistically significant increase in chromosomal aberrations compared to the negative solvent control.
- Hooberman,Brezzell,Das,You,Sinsheimer
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- Electrochemical reduction of certain fluorenyl and xanthenyl olefins
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The reduction of certain fluorene and xanthene containing olefins at a mercury electrode using cyclic voltammetry has been investigated.In DMF, fluorene-9-(4-nitrophenyl)methylene (1) reveals two distinct reversible one-electron redox waves corresponding to anion radical and dianion formation.Some other olefins particularly stilbenes (9-14) and substituted propenones (7,8) show commonality in the emergence of at least one distinct reversible reduction couple.Anion radicals of nearly all of the olefins (1-14) studied in this work generated electrochemically or by chemical 1-electron reductants, exhibited considerable stability.
- Handoo, Kishan L,Kaul, Anju
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p. 579 - 583
(2007/10/02)
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- REACTIONS AT HIGH PRESSURE, PART 18; VOLUMES OF ACTIVATION AND OF REACTION FOR THE WITTIG REACTION
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Volumes of activation have been obtained from rate measurements between 1 and 1000 bar of reactions between triphenyl-p-nitrobenzylidenephosphorane and a series of substituted benzaldehydes.Values of ΔVexcit. lie in the range -20 to -30 cm3mol-1 and are somewhat solvent-dependent.These measurements are in agreement with the accepted reaction mechanism and suggest that the scope of the reaction may be extended by the use of high pressures.
- Isaacs, Neil S.,Abed, Obeid Hassan
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p. 995 - 996
(2007/10/02)
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- Application of Phase-Transfer Catalysis to the Synthesis of Mono- and Bis-stilbenes and Styryls
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A novel and convenient method has been developed for the synthesis of substituted stilbenes by the condensation of active methyl group in suitably substituted toluenes with aromatic aldehydes in aq. medium at room temperature using benzyltriethylammonium chloride as a phase-transfer catalyst.This method has also been applied for the preparation of heterocyclic styryls and extended to the synthesis of bis-stilbenes and bis-styryls using aromatic dialdehydes in place of monoaldehydes.A comparison of the results shows that the present method is superior to the conventional methods in many respects.
- Lokhande, S. B.,Rangnekar, D. W.
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p. 485 - 488
(2007/10/02)
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