20359-74-4

Upstream product

• 611-94-9 4-Methoxybenzophenone 
• 38395-64-1 4-methoxybenzophenone hydrazone 

Downstream Products

• 67444-59-1 2-(4-methoxy-phenyl)-2-phenyl-5,5-bis-trifluoromethyl-2,5-dihydro-[1,3,4]oxadiazole 
• 14845-81-9 p-methoxydiphenylmethylene 
• 429677-33-8 (p-anisyl)phenylmethyl cation 
• 82820-06-2 C₂₂H₁₇N₃O₃ 
• 94866-76-9 4-methoxybenzhydryl benzoate 
• 71350-88-4 4-methoxybenzophenone azine 
• 611-94-9 4-Methoxybenzophenone 
• 7364-21-8 1-methoxy-4-(methoxy(phenyl)methyl)benzene 
• 208332-19-8 pentacarbonyl[(4-methoxyphenyl)phenylcarbene]chromium(O) 
• 26416-50-2 Dithiocarbonic acid S-[isopropoxythiocarbonylsulfanyl-(4-methoxy-phenyl)-phenyl-methyl] ester O-isopropyl ester 
• 26416-44-4 -bis-ethylxanthogenat 
• 1160295-35-1 (4-methoxyphenyl)(phenyl)methyl phenyl sulfone 

Relevant academic research and scientific papers

Stereoelectronic effects in diastereoselective formation of fulleroids

The substituent effects on diastereoselective formation of fulleroids in the reactions of C60 with various unsymmetrical diazoalkanes were investigated. The steric demand on the stereochemical course of reactions dominated the diastereoselectiv

Copper-Catalyzed Oxidation of Hydrazones to Diazo Compounds Using Oxygen as the Terminal Oxidant

A mild method for accessing diazo compounds via aerobic oxidation of hydrazones is described. This catalytic transformation employs a Cu(OAc)2/pyridine catalyst and molecular oxygen from ambient air as the terminal oxidant, generating water as the sole byproduct and affording the desired diazo compounds within minutes at room temperature. A broad array of electronically diverse aryldiazo esters, ketones, and amides can be accessed. Pyridine dramatically enhances the rate of the reaction by solubilizing the copper catalyst and serving as the Br?nsted base in the turnover-limiting proton-coupled oxidation of hydrazone by copper(II). Insights gained from mechanistic studies led to expansion of the scope of this method to include diaryl hydrazones, delivering diaryl diazomethane derivatives, which cannot be accessed via established diazo transfer methods. The products of this method may be employed in rhodium carbene catalysis without isolation of the diazo intermediate to afford cyclopropane products in good yield with high enantioselectivity.

Copper-Mediated Cross-Coupling of Diazo Compounds with Sulfinates

A copper-mediated cross-coupling reaction between a diazo compound and a sodium alkane(arene)sulfinate gives a sulfone as the product. This reaction proceeds under mild conditions and features excellent functional group compatibility. A wide range of sodium alkane(arene)sulfinates were successfully applied in this chemistry. Mechanistic studies revealed that the overall reaction efficiency of the sulfinates was in line with their nucleophilicity in this reaction.

Enantioselective Diarylcarbene Insertion into Si-H Bonds Induced by Electronic Properties of the Carbenes

Catalytic enantioselection usually depends on differences in steric interactions between prochiral substrates and a chiral catalyst. We have discovered a carbene Si-H insertion in which the enantioselectivity depends primarily on the electronic characteristics of the carbene substrate, and the log(er) values are linearly related to Hammett parameters. A new class of chiral tetraphosphate dirhodium catalysts was developed; it shows excellent activity and enantioselectivity for the insertion of diarylcarbenes into the Si-H bond of silanes. Computational and mechanistic studies show how the electronic differences between the two aryls of the carbene lead to differences in energies of the diastereomeric transition states. This study provides a new strategy for asymmetric catalysis exploiting the electronic properties of the substrates.

gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors

A new olefination protocol for transition-metal-free cross-coupling of two carbene fragments arising from two different sources, namely, a nonfluorinated carbene fragment resulting from a diazo compound and a difluorocarbene fragment derived from Ruppert-Prakash reagent (TMSCF3) or TMSCF2Br, has been developed. This gem-difluoroolefination proceeds through the direct nucleophilic addition of diazo compounds to difluorocarbene followed by elimination of N2. Compared to previously reported Cu-catalyzed gem-difluoroolefination of diazo compounds with TMSCF3, which possesses a narrow substrate scope due to a demanding requirement on the reactivity of diazo compounds and in-situ-generated CuCF3, this transition-metal-free protocol affords a general and efficient approach to various disubstituted 1,1-difluoroalkenes, including difluoroacrylates, diaryldifluoroolefins, as well as arylalkyldifluoroolefins. In view of the ready availability of diazo compounds and difluorocarbene reagents and versatile transformations of 1,1-difluoroalkenes, this new gem-difluoroolefination method is expected to find wide applications in organic synthesis.

Cu(I)-catalyzed coupling of diaryldiazomethanes with terminal alkynes: An efficient synthesis of tri-aryl-substituted allenes

A highly efficient method for the synthesis of tri-aryl-substituted allenes has been developed through Cu(I)-catalyzed coupling of diaryldiazomethanes with terminal alkynes. The reaction is under mild conditions and uses simple and inexpensive CuI as the catalyst. Mechanistically, the reaction follows a pathway involving Cu(I) carbene migratory insertion.

Cross-Coupling between Difluorocarbene and Carbene-Derived Intermediates Generated from Diazocompounds for the Synthesis of gem-Difluoroolefins

Cross-coupling between difluorocarbene and carbene-derived intermediates generated from diazocompounds was developed to give gem-difluoroolefins, which constitutes a fast practical pathway to achieve hindered gem-difluoroolefins. The cross-coupling between difluorocarbene and aryl diazoacetates proceeded smoothly in the presence of a copper source, whereas its coupling with diaryl diazomethanes occurred well under metal-free conditions. A mechanism involving a copper-difluorocarbene complex was proposed.