147344-86-3

Upstream product

• 392-83-6 o-trifluoromethylphenyl bromide 
• 536-74-3 phenylacetylene 
• 444-29-1 2-iodo(trifluoromethyl)benzene 
• 312-96-9 2-(trifluoromethyl)benzoyl fluoride 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 433-97-6 2-trifluoromethylbenzoic acid 
• 250643-76-6 tris((2-phenyl)ethynyl)indium 
• 108-86-1 bromobenzene 
• 201230-82-2 carbon monoxide 
• 637-44-5 phenylpropyolic acid 
• 579-76-0 C₇H₄F₃IMg 
• 591-50-4 iodobenzene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 704-41-6 1-ethynyl-2-(trifluoromethyl)benzene 

Downstream Products

• 862604-41-9 CF₃C₆H₄CSn(C₄H₉)3CHC₆H₅ 
• 1186294-03-0 1-phenyl-2-(2-(trifluoromethyl)phenyl)ethane-1,2-dione 

Relevant academic research and scientific papers

Gold(I) iodide catalyzed sonogashira reactions

Gold(I) iodide catalyzed Sonogashira reactions have been developed. Terminal alkynes reacted with aryl iodides and bromides smoothly in the presence of AuI (1 mol-%) and dppf (1 mol-%) in toluene to generate the corresponding cross-coupling products in good to excellent yields. Furthermore, aromatic terminal alkynes could also react with 2-iodoaniline to form substituted indoles in excellent yields through a coupling-cyclization reaction sequence under the present reaction conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

γ-Valerolactone as an alternative biomass-derived medium for the Sonogashira reaction

γ-Valerolactone (GVL) can be used as an efficient and practical alternative to the banned and commonly used dipolar aprotic solvents. In this contribution GVL has been used as a non-toxic, biodegradable, biomass-derived medium, for the definition of a sim

Catalytic efficiency of a new tridentate ferrocenyl phosphine auxiliary: Sonogashira cross-coupling reactions of alkynes with aryl bromides and chlorides at low catalyst loadings of 10-1 to 10-4 Mol %

(Chemical Equation Presented) The catalytic activity in Sonogashira cross-coupling reactions of alkynes with a variety of aryl halides (including chlorides) using a multidentate ferrocenyl phosphine is presented. The novel mixed ferrocenyl aryl/alkyl trip

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.

Decarbonylative Sonogashira Cross-Coupling of Carboxylic Acids

Decarbonylative Sonogashira cross-coupling of carboxylic acids by palladium catalysis is presented. The carboxylic acid is activated in situ by the formation of a mixed anhydride and further decarbonylates using the Pd(OAc)2/Xantphos system to provide an aryl-Pd intermediate, which is intercepted by alkynes to access the traditional Pd(0)/(II) cycle using carboxylic acids as ubiquitous and orthogonal electrophilic cross-coupling partners. The methodology efficiently constructs new C(sp2)-C(sp) bonds and can be applied to the derivatization of pharmaceuticals. Mechanistic studies give support to decarbonylation preceding transmetalation in this process.

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.

Porous organic polymer with: In situ generated palladium nanoparticles as a phase-transfer catalyst for Sonogashira cross-coupling reaction in water

A new Pd nanoparticle loaded and imidazolium-ionic liquid decorated organic polymer of Pd@PTC-POP was readily fabricated via a Pd(PPh3)4 catalysed in situ one-pot Suzuki cross-coupling reaction between imidazolium attached dibromoben

A palladium catalyzed aryl alkyne preparation method

The invention discloses a palladium catalyzed aryl alkyne of the preparation method, comprises the following steps: in the catalyst, under the action of the ligand and alkali, substituted with aryl sulfonyl chloride alkynoic occurs in the organic solvent escapes suosuo the coupling reaction, after the reaction is finished after treatment to obtain the aryl alkyne. Used in the preparation method of the cheap raw material, the reaction and simple post treatment operation, at the same time, the reaction less side reaction, high yield of the product.

A phosphine-free, atom-efficient cross-coupling of aryl iodides with triarylindiums or trialkynylindiums catalyzed by immobilization of palladium(0) in MCM-41

The first phosphine-free heterogeneous atom-efficient cross-coupling reaction of aryl iodides with triarylindiums or trialkynylindiums was achieved in THF at 68 °C by using 1 mol% of MCM-41-immobilized palladium(0)-Schiff base complex [MCM-41-N,N-Pd(0)] as catalyst, yielding a variety of unsymmetrical biaryls and arylalkynes in good to excellent yields. The heterogeneous palladium(0) catalyst could easily be prepared via a simple procedure from commercially readily available reagents, and recovered by filtration of the reaction solution and recycled at least 10 times without significant loss of activity.

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.