4381-02-6

Upstream product

• 15945-07-0 2,4,5-trichlorobenzensulfonyl chloride 
• 26104-68-7 (p-cyanobenzyl)triphenylphosphonium bromide 
• 927-83-3 di-t-butyldiazene 
• 104-85-8 para-methylbenzonitrile 
• 108-88-3 toluene 
• 17201-43-3 4-cyanobenzyl bromide 
• 98-59-9 p-toluenesulfonyl chloride 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 691-38-3 (Z)-4-methyl-2-pentene 
• 110-82-7 cyclohexane 
• 70135-28-3 (4-cyanophenyl)diazomethane 
• 33731-84-9 2,3-bis-(4-bromophenyl)propionic acid 

Downstream Products

• 1220-08-2 bibenzyl-4,4'-dicarbaldehyde 
• 146699-24-3 N-{2-[2-(2-Acetylamino-4-carbamimidoyl-phenyl)-ethyl]-5-carbamimidoyl-phenyl}-acetamide 
• 146699-25-4 1,2-Bis(4-amidino-2-hydroxyphenyl)ethane 
• 146699-22-1 1,2-Bis(4-amidino-2-nitrophenyl)ethane 
• 118463-37-9 1,2-Bis(2-acetamido-4-cyanophenyl)ethane 
• 118463-38-0 1,2-Bis(4-cyano-2-hydroxy-phenyl)ethane 
• 118463-36-8 1,2-Bis(2-amino-4-cyanophenyl)ethane 
• 118463-35-7 1,2-Bis(4-cyano-2-nitro-phenyl)ethane 
• 35872-68-5 bibenzyl-4,4'-bis-carboxamidine 
• 793-07-7 4,4'-(ethene-1,2-diyl)dibenzoic acid 

Relevant academic research and scientific papers

Salt-Stabilized Silylzinc Pivalates for Nickel-Catalyzed Carbosilylation of Alkenes

We herein report the preparation of solid and salt-stabilized silylzinc pivalates from the corresponding silyllithium reagents via transmetalation with Zn(OPiv)2. These resulting organosilylzinc pivalates show enhanced air and moisture stability and unique reactivity in the silylative difunctionalization of alkenes. Thus, a practical chelation-assisted nickel-catalyzed regioselective alkyl and benzylsilylation of alkenes has been developed, which provides an easy method to access alkyl silanes with broad substrate scope and wide functional group compatibility. Kinetic experiments highlight that the OPiv-coordination is crucial to improve the reactivity of silylzinc pivalates. Furthermore, late-stage functionalizations of druglike molecules and versatile modifications of the products illustrate the synthetical utility of this protocol.

Reactions of benzyltriphenylphosphonium salts under photoredox catalysis

The development of benzyltriphenylphosphonium salts as alkyl radical precursors using photoredox catalysis is described. Depending on substituents, the benzylic radicals may couple to form C-C bonds or abstract a hydrogen atom to form C-H bonds. A natural product, brittonin A, was also synthesized using this method.

Photo-catalytic preparation method of bibenzyl compounds

The invention relates to a preparation method of bibenzyl compounds. A compound represented by a formula (A) and a compound represented by a formula (C) carry out reactions under the action of an organic tungsten catalyst and an alkali in the presence of light to generate bibenzyl compounds represented by the formula (B). The method is simple and is easy to operate. The yield is high, and the application range is wide. Moreover, the invention also provides an application of a tungsten complex in organic chemical reactions as a photocatalyst.

Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions

The realization of photocatalysis for practical synthetic application hinges on the development of inexpensive photocatalysts which can be prepared on a large scale. Herein an air-stable, visible-light-absorbing photoluminescent tungsten(vi) complex which can be conveniently prepared at the gram-scale is described. This complex could catalyse photochemical organic transformation reactions including borylation of aryl halides, such as aryl chloride, reductive coupling of benzyl bromides for C-C bond formation, reductive coupling of phenacyl bromides, and decarboxylative coupling of redox-active esters of alkyl carboxylic acid with high product yields and broad functional group tolerance.

Synthesis of dimeric molecules via ag-catalyzed electrochemical homocoupling of organic bromides paired with electrooxidation of urea

We present a sacrificial anode-free approach to reductive homocoupling of organohalides that does not require a co-catalyst. In this approach, a divided electrochemical cell with aprotic and aqueous compartments separated by an anion exchange membrane enables coupling of the cathodic homocoupling reaction with anodic oxidation of urea. We show that, in contrast with traditional one-compartment cells relying on sacrificial anodes, the proposed cell configuration maintains stable cell voltage in the course of galvanostatic electrolysis. A synthetic potential of this method was assessed using a series of 13 organic bromides that demonstrated a strong dependence of the reaction outcome on the structure of the organic substrate, more specifically, the dissociation energy of the C–Br bond and the redox properties of formed radicals, which are discussed in detail. While not being suitable for the synthesis of byarylstructures, this method is excellent for C(sp3)-C(sp3) coupling to corresponding dimeric products with up to quantitative yields. Simultaneous electrochemical treatment of nitrogenous waste in the adjacent half-cell provides an additional incentive for wide adaptation of this sustainable synthetic approach.

Ni(II)/Al(0) mediated benzylic Csp 3 - Csp 3 coupling in aqueous media

Abstract : The reaction of benzyl bromides and chlorides with aluminium metal powder or foil (1.2 eqv.) in the presence of catalytic nickel nitrate (10 mol%) in water at room temperature resulted in homocoupling to the corresponding bibenzyl products which were isolated in moderate to good yields. In sharp contrast, the same reaction in organic solvents like dichloromethane, dimethylformamide, acetonitrile, methanol and toluene yielded only a trace amount of the desired product. The scope of the reaction was tested with substituents on the aromatic ring such as Me-, Cl-, CN-, F-, NO 2-, Ph- as well as 2 ° benzyl halides. Graphical abstract: The reagent combination of aluminium metal and catalytic Ni(NO3)2 promotes the homocoupling of benzyl bromides and chlorides giving rise to the corresponding bibenzyl products in good to excellent yields. The reaction is greatly facilitated in water and showed good functional group tolerance. Besides the mild reaction condition and bench-friendliness, the present reaction constitutes the first example of aluminium-mediated homocoupling of a halide in water. [Figure not available: see fulltext.].

Dual copper- and photoredox-catalysed C(sp2)-C(sp3) coupling

The use of copper catalysis with visible light photoredox catalysis in a cooperative fashion has recently emerged as a versatile means of developing new C-C bond forming reactions. In this work, dual copper and photoredox catalysis is exploited to effect C(sp2)-C(sp3) cross-couplings between aryl boronic acids and benzyl bromides.

Dimerization of Benzyl and Allyl Halides via Photoredox-Mediated Disproportionation of Organozinc Reagents

Benzyl and allyl halides undergo homocoupling when treated with zinc in the presence of a catalytic amount of a cationic iridium(III) complex under irradiation with 400 nm light-emitting diodes. The reaction proceeds through the intermediate formation of an organozinc reagent, which disproportionates to a free radical and elemental zinc under photoredox conditions.

Cyclopentadienyl nickel(ii) N, C-chelating benzothiazolyl NHC complexes: Synthesis, characterization and application in catalytic C-C bond formation reactions

Cyclopentadienyl (Cp) Ni(ii) complexes [CpNiL][PF6] containing hybrid N,C chelating benzothiazolyl NHC ligands (L1 = 1-(2-benzothiazolyl)-3-methylimidazol-2-ylidene, 3a; L2 = 1-(2-benzothiazolyl)-3-allylimidazol-2-ylidene, 3b; L3 = 1-(2-benzothiazolyl)-3-benzylimidazol-2-ylidene, 3c) have been synthesized and fully characterized. The catalytic activity of 3a-3c in some C-C bond formation reactions has been examined. They are efficient catalysts for the homo-coupling of benzyl bromide in the presence of MeMgCl at r.t. with good functional group tolerance. Complex 3a is active in the catalytic oxidative homo-coupling of Grignard reagents with 1,2-dichloroethane as an oxidant at r.t.

Photochemical Reductive C–C Coupling with a Guanidine Electron Donor

The metal-free photoinduced reductive C–C coupling reactions of a number of substituted benzyl halides (15 examples) with the organic electron-donor 2,3,5,6-tetrakis(tetramethylguanidino)pyridine are evaluated. Depending on the substituents at the benzyl group, a C–C coupling product yield in the range 50–95 % is achieved. The photochemical benzyl-radical formation by homolytic N–C bond cleavage of the initially formed benzyl-pyridinium salts is the rate-determining step of these reactions. Electron-withdrawing as well as -donating substituents at the phenyl group increase the reaction rate. Quantum chemical computations did not reveal any correlation between either the enthalpy or Gibbs free energy of the N–C bond cleavage step and the experimentally determined first-order rate constants. Instead, the structural difference between the excited state generated by irradiation and the electronic ground state of the pyridinium ions could be used to rationalize the differences in the reaction rates.