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• 91-20-3 naphthalene 
• 828-73-9 pentafluorophenyl hydrazine 
• 580-13-2 2-bromonaphthalene 
• 1582-24-7 pentafluorophenylboronic acid 
• 363-72-4 Pentafluorobenzene 
• 392-56-3 Hexafluorobenzene 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 63735-42-2 sodium naphthalen-2-ylsulfinate 
• 344-04-7 bromopentafluorobenzene 
• 32316-92-0 naphthalene-2-boronic acid 
• 4830-57-3 pentafluoro sodium benzoate 
• 2243-83-6 2-naphthaloyl chloride 
• 4541-70-2 2-naphthyllithium 
• 93-09-4 naphthalene-2-carboxylate 

Relevant academic research and scientific papers

Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry

The Suzuki–Miyaura cross-coupling between polyfluorinated arylboron nucleophiles and aryl halides enables the efficient construction of polyfluorinated structural motifs frequently found in organic materials and catalysts. A key challenge associated with

Palladium-catalyzed decarbonylative and decarboxylative cross-coupling of acyl chlorides with potassium perfluorobenzoates affording unsymmetrical biaryls

This paper describes the synthesis of unsymmetrical biaryls by the palladium-catalyzed cross-coupling reaction of acyl chlorides with potassium perfluorobenzoates. This transformation is unique in that it involves simultaneous decarbonylation and decarbox

Transition-Metal-Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles

A chemoselective C(sp2)?C(sp2) coupling of sufficiently electron-deficient fluorinated arenes and functionalized N-aryl-N’-silyldiazenes as masked aryl nucleophiles is reported. The fluoride-promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (SNAr). These reactions typically proceed at room temperature within minutes. This catalytic process allows for the functionalization of both coupling partners, furnishing highly fluorinated biaryls in good yields.

Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling

Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chemistry. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetallation of the copper–aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation.

Copper-Catalyzed Defluorinative Hydroarylation of Alkenes with Polyfluoroarenes

A catalytic defluorinative hydroarylation of alkenes with polyfluoroarenes in the presence of dppbz-ligated Cu catalyst and silanes was developed. This method provides a straightforward and alternative avenue to synthetic important polyfluorinated arenes with readily available and bench-stable alkenes as latent nucleophiles, and therefore avoids conventional reliance on stoichiometric quantities of organometallic reagents. This reaction proceeds under very mild conditions and exhibits good functional group compatibility and high level of regioselectivity. The synthetic potential of this method was further demonstrated by a gram-scale synthesis, and an array of experimental studies were also carried out to elaborate the probable mechanism.

Copper-Catalysed Suzuki-Miyaura Cross-Coupling of Highly Fluorinated Aryl Boronate Esters with Aryl Iodides and Bromides and Fluoroarene?Arene π-Stacking Interactions in the Products

A combination of copper iodide and phenanthroline as the ligand is an efficient catalyst for Suzuki-Miyaura cross-coupling of highly fluorinated boronate esters (aryl?Bpin) with aryl iodides and bromides to generate fluorinated biaryls in good to excellent yields. This method represents a nice alternative to traditional cross-coupling methods which require palladium catalysts and stoichiometric amounts of silver oxide. We note that π???π stacking interactions dominate the molecular packing in the partly fluorinated biaryl crystals investigated herein. They are present either between the arene and perfluoroarene, or solely between arenes or perfluoroarenes, respectively.

Ni-Catalyzed Decarboxylative Cross-Coupling of Potassium Polyfluorobenzoates with Unactivated Phenol and Phenylmethanol Derivatives

A Ni-catalyzed decarboxylative cross-coupling of potassium polyfluorobenzoates with unactivated phenol and phenylmethanol derivatives is described. This novel transformation provides a practical and efficient protocol towards the synthesis of important polyfluorobiaryls and polyfluorinated diarylmethanes, and greatly enlarges the range of electrophiles utilized in decarboxylative coupling. Remarkably, preliminary mechanistic studies indicated the essential role of Zn(OAc)2 might lie in the enhancement of decarboxylation step. (Figure presented.).

Palladium-Catalyzed Carbon–Fluorine and Carbon–Hydrogen Bond Alumination of Fluoroarenes and Heteroarenes

Through serendipitous discovery, a palladium bis(phosphine) complex was identified as a catalyst for the selective transformation of sp2C?F and sp2C?H bonds of fluoroarenes and heteroarenes to sp2C?Al bonds (19 examples, 1

Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis

Visible light and eosin Y catalyze the direct arylation of simple arenes with fluorinated aryl bromides by a photoredox process. The reaction scope is broad in fluorinated compounds and arenes and the general and simple procedure provides a metal-free alt

C-O/C-H Coupling of Polyfluoroarenes with Aryl Carbamates by Cooperative Ni/Cu Catalysis

Cross-coupling of polyfluoroarenes with aryl carbamates through the cleavage of both sp2 C-O and C-H bonds is reported. The reaction conditions are simple, and only transition-metal catalysts and ligands are essential. Mechanistic studies indicated that Ni catalyst played an important role in activating C-O bond, while the Cu one in activating C-H Bond. The developed system proved to be effective for cross-coupling of terminal alkynes with aryl carbamates.