65016-20-8

Upstream product

• 591-17-3 meta-bromotoluene 
• 766-97-2 4-n-methylphenylacetylene 
• 29835-27-6 3-(3-methylphenyl)prop-2-ynoic acid 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 33675-43-3 1-(bromo-ethynyl)-3-methyl-benzene 
• 112176-19-9 triisopropoxy(4-methylphenyl)titanium 
• 108-41-8 1-chloro-3-methylbenzene 
• 766-82-5 1-ethynyl-3-methyl-benzene 
• 98-59-9 p-toluenesulfonyl chloride 
• 106-38-7 para-bromotoluene 
• 625-95-6 3-Iodotoluene 
• 106-43-4 para-chlorotoluene 
• 4714-37-8 1-(2,2-dichlorovinyl)-4-methylbenzene 
• 26919-48-2 tri-m-tolylbismuth 

Relevant academic research and scientific papers

Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organotitanium reagents

A Highly efficient route for the synthesis of 1,2-disubstituted acetylene derivatives has been developed by nickel catalyzed cross-couplings of alkynyl halides with aryl titanium reagents under mild conditions. This has given corresponding cross-coupling products good to excellent isolated yields of up to 92 %. The aryls bearing electron-donating or electron-withdrawing groups in either alkynylhalides or aryltitanium substrates gave cross-coupling products good yields. This process was simple and easily performed, which provides an efficient method for the synthesis of 1,2-disubstituted acetylenes derivatives.

Magnetic chitosan-functionalized cobalt-NHC: Synthesis, characterization and catalytic activity toward Suzuki and Sonogashira cross-coupling reactions of aryl chlorides

Aryl chlorides are one of the most stable and available electrophiles, however, their coupling with nucleophiles remains a challenge in organic synthesis. Herein, we prepared a Cobalt-NHC (N-Heterocyclic carbene) complex anchored on magnetic chitosan nanoparticles and assayed its catalytic activity for the reactions of substituted phenylboronic acid and also phenlacetylene with derivatives of aryl chlorides. These reactions are of great importance since they are employed for the synthesis of unsymmetrical diarylethynes and biphenyls, which belong to a prime class of building blocks. The synthesized nanocatalyst was found to be highly efficient in Suzuki and Sonogashira coupling in terms of their activity and recyclability in polyethylene glycol (PEG) as a green reaction media under conditions of temperatures (70 and 100 °C) and Co loading (3 and 6 mol%). To the best of our knowledge, this is the first attempt of using cobalt-NHC complex for catalyzing the abovementioned reactions. Moreover, replacing the earth-abundant Cobalt-based catalyst as an alternative to high cost palladium make this approach promising from sustainable chemistry view.

Green synthesis of graphene oxide (GO)-anchored Pd/Cu bimetallic nanoparticles using: Ocimum sanctum as bio-reductant: An efficient heterogeneous catalyst for the Sonogashira cross-coupling reaction

To explore the synergism between two metal centers we have synthesized graphene oxide (GO) supported Pd/Cu?GO, Pd?GO and Cu?GO nanoparticles through bio-reduction of Pd(NO3)2 and CuSO4·5H2O using Tulsi (Ocimum sanctum) leaf extract as the reducing and stabilizing agent. The graphene oxide (GO) was obtained by oxidation of graphite following a simplified Hummer's method. The as-prepared nanomaterials have been extensively characterized by FTIR, powder X-ray diffraction (PXRD), HRTEM, TEM-EDS, XPS, ICP-AES and BET surface area measurement techniques. The morphological study of Pd/Cu?GO revealed that crystalline bimetallic alloy type particles were dispersed on the GO layer. The activity of Pd?GO, Cu?GO and Pd/Cu?GO as catalysts for the Sonogashira cross-coupling reaction have been investigated and it was found that the Pd/Cu?GO nanostructure showed highly superior catalytic activity over its monometallic counterparts, substantiating the cooperative influence of the two metals. The inter-atom Pd/Cu transmetalation between surfaces was thought to be responsible for its synergistic activity. The catalyst showed higher selectivity towards coupling of aryl iodides with both aliphatic and aryl alkynes resulting in moderate to excellent isolated yield of the desired products (45-99%). The products have been characterized by GC-MS and 1H-NMR spectroscopic techniques and compared with authentic samples. The Pd/Cu?GO catalyst could be easily isolated from the reaction products and reused for up to at least ten successive runs effectively.

Agro waste derived nanosilica supported Pd(ll) complex: A protocol for copper free Sonogashira reaction in water

A palladium (II) complex immobilized onto nanosilica(Pd-imine@nanoSiO2) has been developed and evaluated as a highly efficient, retrievable catalyst for carbon-carbon triple bond activation reactions between aryl halides and terminal alkynes. Nanosilica has been derived from rice husk by simple and eco-compatible methodology. The catalyst has been extensively characterized by techniques such as FT-IR, UV–vis, powder XRD, XPS, SEM-EDX, thermogravimetric analysis, BET surface area measurement. The catalyst can be reused for five consecutive runs without compromising much with the activity. Easy preparation, its long shelf life, air-stability, wide substrate scope, ‘in water’ reactions, easy separability and good recyclability make it an ideal system for Sonogashira cross-coupling reaction. Moreover, various alkyne substrates were efficiently cross-coupled with a broad range of aryl iodides and aryl bromides to afford diaryl alkynes, providing improved yields with low catalyst loading in water. This protocol is also suitable for aliphatic alkynes.

Development of a Palladium-Catalyzed Process for the Synthesis of Z-Alkenes by Sequential Sonogashira–Hydrogenation Reaction

A novel and selective sequential one-pot protocol for the synthesis of Z-alkenes via Sonogashira–semihydrogenation is reported. The efficiency of the methodology is increased by utilizing PdCl2/BuPAd2 as homogeneous catalyst for the Sonogashira coupling and subsequently transforming the transition metal complex into a heterogeneous Pd hydrogenation catalyst. This methodology represents one of the rare examples directly combining homogeneous and heterogeneous catalysis.

Palladium-Catalyzed Decarboxylative Coupling Reactions of Propiolic Acid Derivatives and Arylsulfonyl Hydrazide

Arylsulfonyl hydrazides were employed as coupling partners for the decarboxylative coupling reaction of propiolic acid derivatives. When the reaction was conducted using Pd(TFA) 2 (1.0 mol%), dppp (1.0 mol%), and Cu(OAc) 2 (2.4 equiv

Cross-coupling reactivity of 1,1-dichloroalkenes under palladium catalysis: Domino synthesis of diarylalkynes

An efficient synthesis of diarylalkynes was achieved from the domino cross-coupling reaction of 1,1-dichloroalkenes with triarylbismuth reagents under palladium-catalyzed conditions. Under the established palladium protocol, 1,1-dichloroalkenes demonstrated hitherto unknown remarkable cross-coupling reactivity with organometallic triarylbismuth reagents to furnish functionalized diarylalkynes.

Palladium-Catalyzed Desulfitative Cross-Coupling of Arylsulfonyl Hydrazides with Terminal Alkynes: A General Approach toward Functionalized Internal Alkynes

A palladium-catalyzed Sonogashira-type coupling between arylsulfonyl hydrazides and terminal alkynes via Ar(C)-S bond cleavage is disclosed, which enables the general synthesis of functionalized internal alkynes, especially the Br-substituted ones, in good to excellent yields under acid- and base-free conditions.

Nickel nanoparticles supported on reduced graphene oxide sheets: a phosphine free, magnetically recoverable and cost effective catalyst for Sonogashira cross-coupling reactions

In this study, we have developed a cost effective and one-pot strategy for the synthesis of a heterogeneous catalyst consisting of a Ni nanoparticle-reduced graphene oxide composite for Sonogashira cross-coupling reactions. Several characterization tools were employed to characterize the Ni nanoparticle-reduced graphene oxide composite, which indicated that magnetic Ni nanoparticles of a size range of 1-4 nm were uniformly anchored on the reduced graphene oxide nanosheets without using any surfactant or stabilizing agent. Different types of aryl halides and phenylacetylenes were coupled under the optimized reaction conditions with excellent yields to give biphenylacetylenes. The ferromagnetic behaviour of the Ni nanoparticle-graphene composite resulted in it being easily separable from the reaction mixture and the composite was reusable, up to six times, without losing its catalytic activity. The fresh as well as the reused catalyst for the Sonogashira cross-coupling reaction was well characterized using analytical techniques which showed that the Ni nanoparticles were well dispersed on the reduced graphene oxide nanosheets without agglomeration, and the size and morphology of the catalyst remained unchanged after use in the catalytic reaction.

Copper-catalyzed C(sp2)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons

Copper-catalyzed Sonogashira-type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5mol% Cu 5mol%), broad reaction scope a