2913-53-3

Upstream product

• 76-84-6 triphenylmethyl alcohol 
• 917-71-5 deuterated formic acid 
• 1528-27-4 triphenylmethyl potassium 
• 76-83-5 trityl chloride 
• 4303-71-3 triphenylmethyl sodium 
• 95214-58-7 PdCH₂C⁽²⁾H₂C⁽²⁾H₂CH₂(C₆H₅)2PCH₂CH₂P(C₆H₅)2 
• 341-02-6 trityl tetrafluoroborate 
• 16205-84-8 ethyl 3-(trimethylsilyl)propynoate 
• 95214-59-8 RhCH₂C⁽²⁾H₂C⁽²⁾H₂CH₂(C₆H₅)3P(C₅(CH₃)5) 
• 437-18-3 triphenylmethylium hexafluoridoantimonate 

Downstream Products

• 519-73-3 triphenylmethane 

Relevant academic research and scientific papers

Kinetics of the Reaction of Organosilyl Hydrides with Carbenium Ions in an Inert Solvent. Silicocation Intermediacy. Single Electron Transfer versus Synchronous Hydride Transfer

The rate of reduction of carbenium center with various organosilyl hydrides and one organogermyl hydride in methylene chloride solution was studied.Triphenylmethylium and cycloheptatrienylium salts having metal-halogen complex anions were used as the carbenium substrates.Although the net result of the process at silicon and germanium centers is the formal substitution of H- by halide ion originating from the decomposition of halometallate ion, this substitution proceeds stepwise and one or more silicocation (germanium cation) intermediates are formed.It is possible that one of them has a structure of silylenium (germylenium) ion *Si+ (*Ge+), which may be modified by interaction with solvent.The process which occurs at the carbon center is the hydride-transfer reduction.The kinetic data indicate that the single electron transfer pathway involving the radical silicocation intermediate is followed rather than a synchronous H- transfer from silicon to the carbenium center.

A two-state reactivity model explains unusual kinetic isotope effect patterns in C-H bond cleavage by nonheme oxoiron(IV) complexes

It's in the bond: The cleavage of C H bonds by two related oxoiron(IV) complexes shows a range of kinetic isotope effect (KIE) values that exhibit an unusual dependence on the C H bond strength. Large nonclassical KIEs are observed for bond strengths belo

Room-Temperature Palladium-Catalyzed Deuterogenolysis of Carbon Oxygen Bonds towards Deuterated Pharmaceuticals

Site-specific incorporation of deuterium into drug molecules to study and improve their biological properties is crucial for drug discovery and development. Herein, we describe a palladium-catalyzed room-temperature deuterogenolysis of carbon–oxygen bonds

Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules

An efficient catalytic method to convert an α-C-H bond of N-alkylamines into an α-C-alkynyl bond was developed. In the past, such transformations were carried out under oxidative conditions, and the enantioselective variants were confined to tetrahydroisoquinoline derivatives. Here, we disclose a method for the union of N-alkylamines and trimethylsilyl alkynes, without the presence of an external oxidant and promoted through cooperative actions of two Lewis acids, B(C6F5)3 and a Cu-based complex. A variety of propargylamines can be synthesized in high diastereo-and enantioselectivity. The utility of the approach is demonstrated by the late-stage site-selective modification of bioactive amines. Kinetic investigations that shed light on various mechanistic nuances of the catalytic process are presented.

Earth-Abundant Metal Catalysis Enabled by Counterion Activation

A precatalyst activation strategy has been developed for earth-abundant metal catalysis enabled by counterion dissociation and demonstrated through alkene hydroboration. Commercially available iron and cobalt tetrafluoroborate salts were found to catalyze

Method for constructing carbon-hydrogen bond by catalyzing alcohol dehydroxylation with palladium/platinum

The invention discloses a method for constructing a carbon-hydrogen (deuterium) bond. The method comprises the following step: in the presence of a palladium/platinum catalyst and aryl halide, an alcohol hydroxyl group of an alcohol and hydrogen (deuterium) gas is replaced by hydrogen (deuterium) to construct the carbon-hydrogen (deuterium) bond. According to the method, the palladium/platinum catalyst is used as a catalyst, the green hydrogen (deuterium) gas is used as a hydrogen (deuterium) source, efficient alcohol dehydroxylation is performed at room temperature to construct the carbon-hydrogen (deuterium) bond, and the method is particularly suitable for constructing the carbon-deuterium bond and can be widely applied to synthesis of deuterated drugs.

Dehalogenation of organic halides using the NiCl2·2H2O-Li-DTBB (cat.) combination

The reaction of different chlorinated, brominated or iodinated materials, bearing or without a functional group, with a mixture of nickel(II) chloride dihydrate, an excess of lithium powder and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB) (5 mol%) in THF at room temperature, leads to the formation of the corresponding products resulting from a halogen/hydrogen exchange. The use of deuterium oxide instead of water in the nickel salt allows the corresponding deuteration. This methodology does not work with fluorinated materials.

Regiospecific Hydride Abstraction from Metallacycles: Conversion of Metallacyclopentanes to Cationic ?-Allylic Complexes

The rhoda- and irida-cyclopentane complexes (η5-C5Me5)(PPh3)> react with the trityl cation + to give the η3-1-methylallyl derivatives 3-CH2CHCHMe)(η5-C5Me5)(PPh3)>.Deuterium-labelling studies show that in these cases as well as in the previously reported palladacyclopentane->(η3-1-methylallyl)palladium complex transformations, the trityl cation abstracts regiospecifically one of the β-hydrogen atoms of the metallacyclic moiety.The involvement of a ?-3-butenyl intermediate which rearranges to a η3-1-methylallyl derivative is confirmed by reacting the palladium and rhodium dihalides, and 5-C5Me5)(PPh3)I2>, with 3-butenylmagnesium bromide.In the case of palladium a ?-3-butenyl complex is obtained which, by reacting with AgBF4, gives the η3-1-methylallyl derivative 3-CH2CHCHMe)(Ph2PCH2CH2PPh2)>.In the case of rhodium the PPh3 ligand is lost and the η3-1-methylallyl compound 3-CH2CHCHMe)(η5-C5Me5)I> is obtained directly.By reacting 5-C5Me5)(PPh3)I2> with 3-pentanylmagnesium bromide, the η3-1,3-dimethylallyl complex 3-MeCHCHCHMe)(η5-C5Me5)(PPh3)> is obtained.Mechanistic implications are discussed along with the significance of the reactions studied in connection with the role of transition-metal metallacyclopentane derivatives in organometallic chemistry and in catalysis.

Kinetic Hydrogen Isotope Effects in Intermolecular Hydride Transfer from Arylalkanes to 9-Arylfluoren-9-yl Cations

Rates of hydride-ion transfer to a series of 9-phenylfluoren-9-yl cations, substituted in the phenyl group, from triphenylmethane and 4,4'-dimethoxydiphenylmethane have been measured at 30 degC in trifluoroacetic acid solution containing 6percent v/v acet

Organometallic compounds of group III. XXXIV. Steric factors in the carbalumination of olefins. The question of the anomalous, reduced reactivity of olefins versus acetylenes.

In order to understand the reasons for the anomalous, reduced reactivity of olefins toward electrophilic carbalumination, compared with that of acetylenes, the reactivity, stereochemistry and regiochemistry of a series of acyclic and cyclic olefins in carbalumination with triphenylaluminum were investigated. The following substrates underwent reaction between 80 and 225°C with decreasing ease in the order: norbornadiene > cis-β-methylstyrene > trans-β-methylstyrene ～ 1,2-dihydronaphthalene ～ 1,1-dimethylindene > cis-1,2-diphenylethylene > 3,3,3-triphenylpropene > trans-1,2-diaryethylenes ～ phenylcyclopropanes. The stereochemistry of the mono- and bis-carbaluminations of norbornadiene was shown to be syn, exo. The regiochemistry observed with unsymmetrical olefins could readily be rationalized by a steric effect operative in the preferential collapse of an olefin-(C6H5)3Al π-complex. Besides carbalumination, several other reactions were observed with these olefins: (1) cis, trans-isomerization of acyclic olefins; (2) metallation of vinylic carbon atoms by (C6H5)3Al; (3) elimination of (C6H5)2AlH from carbalumination adducts; (4) by inference from the foregoing reaction with certain systems, epimerization at sp3-hybridized carbon-aluminum bonds; and (5) decarbalumination with carbon-carbon bond scission. These side reactions were considered together with relative reactivities, stereochemistry and regiochemistry in developing energy profiles for the carbalumination of olefins and acetylenes. The reduced reactivity of olefins is thought to arise from steric factors that destabilize a π-complex-with (C6H5)3Al and that cause a trapezoidal-like transition state to be of higher energy and rate-determining. The higher reactivity of acetylenes is ascribed to less steric hindrance both to π-complexation with (C6H5)3Al, and to the collapse of the complex via a trapezoidal configuration. For acetylenes, it is judged that the formation of an intimate π-complex is rate-determining.