858344-44-2

Upstream product

• 402-43-7 p-trifluoromethylphenyl bromide 
• 7646-85-7 zinc(II) chloride 
• 455-13-0 4-Iodobenzotrifluoride 
• 7699-45-8 zinc dibromide 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 
• 2786-01-8 (4-trifluoromethylphenyl)lithium 

Downstream Products

• 858344-45-3 (p-CF3C6H4)2Zn2(μ-OCHPr(i)2)2 
• 858344-48-6 (p-CF3C6H4)2Zn3(μ-OCHPr(i)2)4 
• 34239-04-8 1-benzyl-4-(trifluoromethyl)benzene 
• 170789-13-6 1-methyl-4-(4-(trifluoromethyl)benzyl)benzene 
• 1258862-74-6 C₂₅H₁₆BF₆N 
• 1283129-22-5 (2R,3R,4R,5S,6S)-2-(pivaloyloxymethyl)-6-(4-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyltris(2,2-dimethylpropanoate) 
• 460743-71-9 2-(4-(trifluoro-methyl)phenyl)naphthalene 
• 1355041-41-6 3-hydroxy-2-phenyl-3-(4-(trifluoromethyl)phenyl)isoindolin-1-one 
• 2251-82-3 1-(difluoromethyl)-4-(trifluoromethyl)benzene 

Relevant academic research and scientific papers

Atom-efficient transition-metal-free arylation ofN,O-acetals using diarylzinc reagents through Zn/Zn cooperativity

Exploiting the cooperative action of Lewis acid Zn(C6F5)2with diarylzinc reagents, the efficient arylation ofN,O-acetals to access diarylmethylamines is reported. Reactions take place under mild reaction conditions without the need for transtion-metal catalysis. Mechanistic investigations have revealed that Zn(C6F5)2not only acts as a Lewis acid activator, but also enables the regeneration of nucleophilic ZnAr2species, allowing a limiting 50 mol% to be employed.

Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes

Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, aminohalogenation and aminocarbonation of readily available cyclohexenyl triflates. We have demonstrated the novel use of zincate base/nucleophile system for effective formation of key cyclohexyne intermediates and selective addition of various carbon and nitrogen nucleophiles. Importantly, leveraging the resulting organozincates enables the incorporation of a broad range of electrophilic partners to deliver structurally diverse cyclohexene motifs. The importance and utility of this method is also exemplified by the modularity of this approach and the ease in which even highly complex polycyclic scaffolds can be accessed in one step.

SALT, ACID GENERATOR, RESIST COMPOSITION AND METHOD FOR PRODUCING RESIST PATTERN

Disclosed are a salt represented by formula (1), and an acid generator and a resist composition which include the same: wherein R1 represents a fluorine atom or a fluorinated alkyl group; R2, R3 and R4 each represent a halogen atom, a fluorinated alkyl group or a hydrocarbon group; m2 and m3 represent an integer of 0 to 4; m4 represents an integer of 0 to 5; Q1 and Q2 each represent a fluorine atom or a perfluoroalkyl group; L1 represents a saturated hydrocarbon group, —CH2- included in the group may be replaced by —O— or —CO—, and a hydrogen atom included in the group may be substituted with a fluorine atom or a hydroxy group; Y1 represents a methyl group which may have a substituent or an alicyclic hydrocarbon group which may have a substituent.

CARBOXYLATE, CARBOXYLIC ACID GENERATOR, RESIST COMPOSITION AND METHOD FOR PRODUCING RESIST PATTERN

Disclosed are a carboxylate represented by formula (I), and a carboxylic acid generator and a resist composition, including the same: wherein R1 represents a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms; R2, R3 and R4 each independently represent a halogen atom, a fluorinated alkyl group having 1 to 4 carbon atoms or a hydrocarbon group having 1 to 12 carbon atoms, and —CH2— included in the hydrocarbon group may be replaced by —O— or —CO—; m2 and m3 represent an integer of 0 to 4, and m4 represents an integer of 0 to 5; and X0 represents a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and —CH2— included in the hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO2—.

One-pot Negishi cross-coupling reaction of aryldiazonium salts via Ni catalysis induced by visible-light

Visible-light induced catalysis is of high interest for its mild and environmentally benign properties. Herein, a general Ni catalysis accelerated by visible-light was successfully developed for one-pot Negishi coupling reactions at room temperature in a short reaction time (2Zn generated in situ from Grignard reagents and ZnBr2. This protocol provides a convenient access to C–C bond formation for important biaryl components. It tolerates various functional groups, and Hammett study illuminates the possiblility of Ni(III)/Ni(I) redox catalytic cycle.

Vinyl Carbocations Generated under Basic Conditions and Their Intramolecular C-H Insertion Reactions

Here we report the surprising discovery that high-energy vinyl carbocations can be generated under strongly basic conditions, and that they engage in intramolecular sp3 C-H insertion reactions through the catalysis of weakly coordinating anion salts. This approach relies on the unconventional combination of lithium hexamethyldisilazide base and the commercially available catalyst, triphenylmethylium tetrakis(pentafluorophenyl)borate. These reagents form a catalytically active lithium species that enables the application of vinyl cation C-H insertion reactions to heteroatom-containing substrates.

Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents

This work bridges a gap in the cross-coupling of aliphatic redox-active esters with aryl zinc reagents. Previously limited to primary, secondary, and specialized tertiary centers, a new protocol has been devised to enable the coupling of general tertiary systems using nickel catalysis. The scope of this operationally simple method is broad, and it can be used to simplify the synthesis of medicinally relevant motifs bearing quaternary centers.

Exploiting Synergistic Effects in Organozinc Chemistry for Direct Stereoselective C-Glycosylation Reactions at Room Temperature

Pairing a range of bis(aryl) zinc reagents ZnAr2 with the stronger Lewis acidic [(ZnArF2)] (ArF=C6F5), enables highly stereoselective cross-coupling between glycosyl bromides and ZnAr2 without the use of a transition metal. Reactions occur at room temperature with excellent levels of stereoselectivity, where ZnArF2 acts as a non-coupling partner although its presence is crucial for the execution of the C(sp2)–C(sp3) bond formation process. Mechanistic studies have uncovered a unique synergistic partnership between the two zinc reagents, which circumvents the need for transition-metal catalysis or forcing reaction conditions. Key to the success of the coupling is the avoidance of solvents that act as Lewis bases versus diarylzinc compounds (e.g. THF).

Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis

A cobalt-catalyzed decarboxylative Negishi coupling reaction of redox-active aliphatic esters with organozinc reagents was developed. The method enabled efficient alkyl–aryl, alkyl–alkenyl, and alkyl–alkynyl coupling reactions under mild reaction conditions with no external ligand or additive needed. The success of an in situ activation protocol and the facile synthesis of the drug molecule (±)-preclamol highlight the synthetic potential of this method. Mechanistic studies indicated that a radical mechanism is involved.

Iron-Catalyzed Difluoromethylation of Arylzincs with Difluoromethyl 2-Pyridyl Sulfone

We report the first iron-catalyzed difluoromethylation of arylzincs with difluoromethyl 2-pyridyl sulfone via selective C-S bond cleavage. This method employs the readily available, bench-stable fluoroalkyl sulfone reagent and inexpensive iron catalyst, allowing facile access to structurally diverse difluoromethylated arenes at low temperatures. The experiment employing a radical clock indicates the involvement of radical species in this iron-catalyzed difluoromethylation process.