82404-39-5

Upstream product

• 455-13-0 4-Iodobenzotrifluoride 
• 766-97-2 4-n-methylphenylacetylene 
• 98-59-9 p-toluenesulfonyl chloride 
• 705-31-7 4-trifluoromethylphenylacetylene 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 350-42-5 4-methylbenzoyl fluoride 
• 40230-95-3 1-(4-trifluoromethylphenyl)-2-trimethylsilylethyne 
• 368-94-5 4-trifluoromethyl-benzoyl fluoride 
• 4186-14-5 1-(2-(trimethylsilyl)ethynyl)toluene 
• 313343-88-3 1-(bromoethynyl)-4-(trifluoromethyl)benzene 
• 112176-19-9 triisopropoxy(4-methylphenyl)titanium 
• 131356-53-1 1-(2,2-dibromovinyl)-4-(trifluoromethyl)benzeney 
• 5720-05-8 4-methylphenylboronic acid 
• 455-19-6 4-Trifluoromethylbenzaldehyde 

Downstream Products

• 86568-05-0 (C₁₀H₄(OH)(C₆H₄CH₃)(C₆H₄CF₃)OCH₃)Cr(CO)3 
• 82421-72-5 (C₁₀H₄(OH)(C₆H₄CF₃)(C₆H₄CH₃)OCH₃)Cr(CO)3 
• 82421-86-1 Tricarbonyl-[1-4:9,10-η6-[4-methoxy-2-(4-methylphenyl)-3-[4-(trifluormethyl)phenyl]-1-naphthol]]chrom(0) 
• 526202-18-6 Cp₂Zr(C₄-2,5-(p-C₆H₄CF₃)2-3,4-(C₆H₄Me)2) 
• 526202-12-0 Cp₂Zr(C₄-3,4-(p-C₆H₄CF₃)2-2,5-(C₆H₄Me)2) 
• 526202-14-2 Cp₂Zr(C₄-3,5-(p-C₆H₄CF₃)2-2,4-(C₆H₄Me)2) 
• 1437733-56-6 (Z)-1,3,5-trimethyl-2-(1-p-tolyl-2-(4-(trifluoromethyl)phenyl)vinyl)benzene 
• 1437733-73-7 (E)-1-methyl-4-(1-phenyl-2-(4-(trifluoromethyl)phenyl)vinyl)benzene 
• 143958-88-7 (E)-1-methyl-4-(4-(trifluoromethyl)styryl)benzene 

Relevant academic research and scientific papers

Electro-alkynylation: Intramolecular Rearrangement of Trialkynylorganoborates for Chemoselective C(sp2)-C(sp) Bond Formation

An alternative and complementary transformation for the synthesis of aryl- and heteroaryl-substituted alkynes is presented that relies on a chemoselective electrocoupling process. Tetraorganoborate substrates were logically designed and simply accessed by transmetalations using readily or commercially available organotrifluoroborate salts.

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.

Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes: Synthesis of unsymmetrical diarylethynes

Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes is described. This reaction not only effectively inhibits the formation of undesired homocoupled products by avoiding the addition of a base, but also exhibits a wide substrate scope to provide a general access to diverse unsymmetrical diarylethynes.

Nickel-Catalyzed Sonogashira C(sp)-C(sp2) Coupling through Visible-Light Sensitization

An efficient method for visible-light-initiated, nickel-catalyzed Sonogashira C(sp)-C(sp2) coupling has been developed via an energy-transfer mode. Thioxanthen-9-one as a photosensitizer could significantly accelerate the arylation of alkynes with a wide

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.

Synthesis of o-Allyloxy(ethynyl)benzene Derivatives by Cu-Catalyzed Suzuki–Miyaura-Type Reaction and Their Transformations into Heterocyclic Compounds

We have found that Suzuki–Miyaura-type reactions of o-allyloxy(bromoethynyl)benzenes with arylboronic acids using a hydrazone/Cu catalyst system proceeded smoothly in iPrOH under mild conditions to afford the corresponding o-allyloxy(arylethynyl)benzene derivatives in good yields without decomposition of the allyloxy group. We have further demonstrated that annulation and enyne metathesis of the o-allyloxy(arylethynyl)benzene derivatives using transition-metal catalysts led to various heterocyclic compounds.

Three-Component One-Pot Synthesis of Unsymmetrical Diarylalkynes by Thermocontrolled Sequential Sonogashira Reactions Using Potassium Ethynyltrifluoroborate

Unsymmetrical diarylalkynes were synthesized in moderate to good yields through a three-component one-pot procedure involving thermocontrolled sequential Sonogashira reactions with potassium ethynyltrifluoroborate and two different reactive aryl halides. The one-pot procedure was initiated by the palladium/copper-catalyzed Sonogashira coupling of potassium ethynyltrifluoroborate to an aryl iodide or electron-deficient aryl bromide at 40 °C. Following a subsequent deboronative Sonogashira reaction of the in situ generated potassium (arylethynyl)trifluoroborate, a second coupling to a less-active electron-rich aryl bromide at 80 °C, without any additional palladium/copper catalyst or base, gave rise to unsymmetrical diarylalkynes.

Palladium Nanoparticles Supported on a Porous Organic Polymer: An Efficient Catalyst for Suzuki-Miyaura and Sonogashira Coupling Reactions

A new porous organic polymer (POP) with high thermal stability and large surface area has been synthesized and applied in the preparation of Pd/POP catalyst. Pd/POP was characterized by XRD, TGA, SEM and TEM. The catalyst consists of highly dispersed palladium nanoparticles of 0.9-4 nm size on POP with a large surface area of 650 m2/g. It presents high catalytic activity for Suzuki-Miyaura and Sonogashira reactions. The catalyst was reusable for three to five times without significant loss of activity. A new porous organic polymer (POP) was synthesized and applied in the preparation of Pd/POP catalyst. Pd/POP exhibits high catalytic activity for Suzuki-Miyaura and Sonogashira reactions and is reusable in these heterogeneous catalytic reactions.

The copper-free Sonogashira cross-coupling reaction promoted by palladium complexes of nitrogen-containing chelating ligands in neat water at room temperature

The commercially available 2,2′-dipyridylamine was used as a supporting ligand in the palladium-catalyzed Sonogashira cross-coupling reaction. The reactions between aryl iodides and terminal alkynes with different steric hindrance can be efficiently performed in the absence of copper in neat water at room temperature. The superior catalytic performance of the catalytic system was attributed to water solubility of the palladium 2,2′- dipyridylamine complex. Palladium nanoparticles with small size and narrow size distribution were formed after the cross-coupling reaction.

Sonogashira/hydroarylation sequential reactions: Catalyzed by NHC-Pd complexes

It was found that an air-stable NHC-palladium complex of Pd[(s)-3-C 3H5-4-(C5H5CH2)-1-(2,6- iPr2C6H3)-C3H 3N2](C5H5N)Br2 derived from l-phenylalanine is an effective pre-catalyst for copper-free and phosphine-free Sonogashira reaction of alkynes under aerobic conditions in short reaction time. Moreover, the palladium compound would be reused to catalyze the hydroarylation of alkyne prepared from Sonogashira reaction, which makes firstly Sonogashira/Hydroarylation sequential reactions successful. The arylation of alkynes underwent with a high regio- and stereoselectivity and only trans-arylation of alkyne was observed. No Z/E isomerization of the olefin was observed in the system.