18206-43-4

Usage

Uses

Used in Organic Synthesis:
Copper, (pentafluorophenyl)is used as a catalyst in cross-coupling reactions and carbon-carbon bond formation, facilitating the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
Copper, (pentafluorophenyl)is used as a catalyst in the preparation of pharmaceuticals, enabling the synthesis of complex drug molecules with improved efficiency and selectivity.
Used in Agrochemical Industry:
Copper, (pentafluorophenyl)is used as a catalyst in the synthesis of agrochemicals, contributing to the development of effective and selective pesticides and other agricultural chemicals.
Used in Materials Science:
Copper, (pentafluorophenyl)is used as a catalyst in the preparation of advanced materials, such as polymers, coatings, and composites, with tailored properties for various applications.
Note: Due to its reactivity and potential toxicity, Copper, (pentafluorophenyl)should be handled and stored with caution.

Upstream product

• 344-07-0 1-chloro-2,3,4,5,6-pentafluorobenzene 
• 344-04-7 bromopentafluorobenzene 
• 1076-44-4 pentafluorophenyl lithium 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 1206-46-8 trimethyl(pentafluorophenyl)silane 
• 363-72-4 Pentafluorobenzene 
• 7681-65-4 copper(l) iodide 
• 879-06-1 pentafluorophenylmagnesium chloride 
• 30123-12-7 silver(I)pentafluorobenzene 

Downstream Products

• 652-23-3 perfluorostyrene 
• 242816-80-4 Re(C₅H₅)(CO)2(C₆F₅)2 
• 242816-74-6 Re(C₅(CH₃)5)(CO)2(C₆F₅)2 
• 923001-31-4 (SC₄H₂B(C₅H₄)Fe(C₅H₅)C₆F₅)2 
• 1078738-56-3 pentafluorophenylcopper-phenanthroline complex 
• 1210318-31-2 sodium tris(pentafluorophenyl)(t-butylphenyl)borate 
• 1286770-03-3 B(C₆Cl₅)(C₆F₅)2 
• 1286770-04-4 B(C₆Cl₅)2(C₆F₅) 
• 923001-35-8 (SC₄H₂B(C₆F₅)2NC₅H₅)2 
• 211636-23-6 bis[(3,5-bis(trifluoromethyl)phenyl)]borinic acid 

Relevant academic research and scientific papers

Photocatalytic Decarboxylative Coupling of Aliphatic N-hydroxyphthalimide Esters with Polyfluoroaryl Nucleophiles

Polyfluoroarenes are an important class of compounds in medical and material chemistry. The synthesis of alkylated polyfluoroarenes remains challenging. Here we describe a decarboxylative coupling reaction of N-hydroxyphthalimide esters of aliphatic carboxylic acids with polyfluoroaryl zinc reagents (Zn-ArF) via synergetic photoredox and copper catalysis. This method readily converts primary and secondary alkyl carboxylic acids into the corresponding polyfluoroaryl compounds, which could have a wide range of F-content (2F-5F) and variable F-substitution patterns on the aryl groups. Broad scope and good functional group compatibility were achieved, including on substrates derived from natural products and pharmaceuticals. Mechanistic study revealed that a [Cu-(ArF)2] species could be responsible for the transfer of polyfluoroaryl groups to the alkyl radicals.

Controllable double CF2-insertion into sp2 C-Cu bond using TMSCF3: A facile access to tetrafluoroethylene-bridged structures

A highly efficient method for controllable double CF2-insertion into pentafluorophenylcopper species using TMSCF3 as difluoromethylene source has been developed. The newly generated fluoroalkylcopper(i) species, C6F5CF2CF2Cu, shows good reactivity towards a myriad of structurally diverse aryl, heteroaryl and alkenyl iodides. This protocol is easy to handle, ready to scale up and applicable for the synthesis of relative complex molecules, thus providing a convenient method for facile access to tetrafluoroethylene-bridged structures.

COPPER-CATALYZED C-H BOND ARYLATION

The present invention is a one-step method for efficiently converting carbon-hydrogen bonds into carbon-carbon bonds using a combination of aryl halides, a substrate, and a copper salt as catalyst. This method allows faster introduction of complex molecular entities, a process that would otherwise require many more steps. This invention is particularly relevant for the organic synthesis of complex molecules such as, but not limited to, pharmacophores and explosives.

A comparative study of base-free arylcopper reagents for the transfer of aryl groups to boron halides

A comparative study on the reactivity and selectivity of arylcopper species in reactions with boron halides was performed. Mesitylcopper reacts with BX3 (X=Cl, Br) in toluene at low temperature under highly selective formation of the monosubstituted boranes MesBX2. The dimesitylboranes Mes2BX are gradually formed with a twofold excess of the organocopper reagent at elevated temperature. In contrast, pentafluorophenylcopper shows a tendency for formation of B(C6F5) 3 in reactions with BX3 irrespective of the stoichiometry used, suggesting a strong impact of electronic factors on the selectivity of the aryl transfer reaction. New procedures for the synthesis of the pentafluorophenylboron halides C6 F5BX2 (X=Cl: 57%; X=Br: 62%) and of tris(pentafluorophenyl)borane (80%) and related mixed-substituted triarylboranes from the base-free isolable pentafluorophenylcopper precursor have been developed.

Photochemical reactions of [Re(η5-C5R5)(CO)3] (R = H or Me) with partially fluorinated benzenes: C-H and C-F activation

UV Irradiation of [Re(η5-C5R5)(CO)3] (R = Me or H) in the presence of C6F5H or 1,2,4,5-C6F4H2 effected intramolecular C-H activation, generating the hydrido complexes trans-[Re(η5-C5R5)(CO)2(Ar) FH] [(Ar)F = C6F5 or 2,3,5,6-C6F4H] as the principal photochemical products. The identities of the hydrido complexes were confirmed by independent thermal syntheses. The photoreaction of [Re(η5-C5Me5)(CO)3] with C6F5H also generated the fulvene complex [Re(η6-C5Me4CH2)(CO) 2(C6F5)] 2a and two bis(aryl) derivatives: cis-[Re(η5-C5Me5)(CO)2(C 6F5)2] 3a and [Re(η5-C5Me5)(CO)2(C 6F5)(2,3,5,6-C6F4H)] 4a in low yield. Complex 2a results from an intramolecular C-H activation, while 3a and 4a derive from a C-H and a C-F activation of a second molecule of pentafluorobenzene, respectively. The origin of the minor products was elucidated by showing that UV irradiation of [Re(η5-C5Me5)(CO)2-(C 6F5)H] in C6F5H produces 2a, 3a and 4a, while photolysis of 2a produces only 3a. The reaction of [Re(η5-C5Me5)-(CO)3] with 1,2,4,5-C6F4H2 gave analogues 2b and 4b as minor products. The photoreaction of [Re(η5-C5H5)(CO)3] in C6F5H or 1,2,4,5-C6F4H2 generated bis(aryl) compounds and the unusual binuclear complexes [Re2(η5-C5H5)(μ-η 1:η5-C5H4)(CO) 4(Ar)F] as the minor products. The binuclear complex with (Ar)F = 2,3,5,6-C6F4H has been characterized by X-ray crystallography. The Re-Re bond [3.0258(7) A] is close to collinear with the Re-C (aryl) bond. One {Re(CO)2} unit is twisted by about 73.0° with respect to the other.