55816-26-7

Upstream product

• 5162-03-8 (2-chlorophenyl)(phenyl)methanone 

Downstream Products

• 55816-20-1 N₂,N₄-Di-(2-chlorphenylmethylen)-formohydrazid-hydrazon 
• 1428979-34-3 4-(3-phenyl-1H-indazole-1-yl)benzonitrile 
• 1428979-29-6 1-(4-methoxyphenyl)-3-phenyl-1H-indazole 
• 13097-01-3 3-phenyl-1H-indazole 
• 135226-12-9 2-chlorodiphenylcarbene 
• 60664-73-5 2-chlorodiphenyldiazomethane 
• 103167-40-4 bis-(2-chloro-benzhydrylidene)-hydrazine 

Relevant academic research and scientific papers

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.

Silver-Catalyzed N-H Functionalization of Aryl/Aryl Diazoalkanes with Anilines

Herein, we report on the N-H functionalization reaction of primary and secondary anilines with diaryldiazoalkanes using simple AgPF6 as catalyst. We demonstrated broad applicability in the reaction of diaryldiazoalkanes with different anilines (31 examples, up to 97% yield). Furthermore, we propose a possible reaction mechanism for the N-H functionalization.

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.

Ni and Cu-catalyzed one pot synthesis of unsymmetrical 1,3-di(hetero)aryl-1: H -indazoles from hydrazine, o -chloro (hetero)benzophenones, and (hetero)aryl bromides

The nickel-catalyzed cyclization of in situ generated ortho-chlorobenzophenone hydrazone derivatives, to afford 3-(hetero)aryl-1H-indazoles, is documented for the first time. The product 1H-indazoles can be transformed subsequently in a one-pot procedure into 1,3-di(hetero)aryl-1H-indazoles via copper-catalyzed N-arylation with (hetero)aryl bromides.

Visible light photocatalytic decarboxylative monofluoroalkenylation of α-amino acids with: Gem -difluoroalkenes

α-Amino acids are among the most common biologically active molecules in nature, and their functionalization has attracted much attention. In this communication, a novel, efficient and general visible-light photocatalytic decarboxylative monofluoroalkenylation of N-protected α-amino acids with gem-difluoroalkenes is reported, affording the corresponding α-amino monofluoroalkenes which might find applications in medical chemistry and materials science. The reaction proceeded at room temperature with high efficiency and tolerance of various functional groups.

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.

Contributions of Quantum Mechanical Tunneling to the Rate of Benzylic Hydrogen Atom Abstractions Reactions of Triplet Diarylcarbenes in Fluid Solution

Kinetic isotope effects for the benzylic hydrogen atom abstraction reactions of the triplet states of several diarylcarbenes with toluene-toluene-d8 in fluid solution were determined by measuring the ratio of 1,2-diphenylethane to 1,2-diphenylethane-d7 pr