158918-48-0

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 158918-39-9 1-(3-bromophenyl)-1-pentanol 
• 847941-40-6 1,2-bis(3-bromophenyl)ethene 
• 20657-38-9 cis-1,2-bis(3-bromophenyl)ethene 
• 1566469-55-3 (Z)-1-bromo-3-(3,3,3-trifluoro-2-phenylprop-1-enyl)benzene 
• 1566469-53-1 (E)-1-bromo-3-(3,3,3-trifluoro-2-phenylprop-1-enyl)benzene 
• 908354-13-2 1-(3-bromophenyl)-1,1-di(phenylseleno)methane 
• 91028-08-9 1-bromo-3-(propa-1,2-dien-1-yl)benzene 
• 1382802-09-6 (1-(3-bromophenyl)but-3-enyl)(phenyl)sulfane 
• 67203-58-1 3-(3-bromophenyl)-5-phenyl-1H-pyrazole 
• 1379610-54-4 2-(3-bromobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 949478-36-8 3-(3-bromophenyl)-1-(4-methoxyphenyl)-(2E)-2-propen-1-one 

Relevant academic research and scientific papers

Potassium tert -Butoxide Promoted Synthesis of 4,5-Diaryl-2 H -1,2,3-triazoles from Tosylhydrazones and Nitriles

Intermolecular cycloaddition of tosylhydrazones with nitriles was investigated. t -BuOK was shown to be an excellent base for increasing the effectiveness of the reaction in this protocol, and homocoupling of the tosylhydrazones was significantly inhibited by using xylene as a solvent. Through this transformation, a variety of 4,5-diaryl-2 H -1,2,3-triazoles were prepared in good to excellent yields and with high purities. The process is azide-free and transition-metal-free.

Palladium-Catalyzed Three-Component Coupling Reaction of o-Bromobenzaldehyde, N-Tosylhydrazone, and Methanol

A ligand-controlled palladium-catalyzed three-component reaction of o-bromobenzaldehyde, N-tosylhydrazone, and methanol is described. This reaction uses readily available compounds as starting materials while displaying a broad substrate scope and good functional group compatibility.

Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay

The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.

Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles

An efficient and practical C–N bond formation methodology for the synthesis of N-alkylated (benzo)thiazoles was developed, via the copper-catalyzed one-pot two-step reactions of 2-amino(benzo)thiazoles and aldehydes (ketones) with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups (46 examples). A variety of functionalized N-alkylated (benzo)thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol.

Rapid Synthesis of N-Tosylhydrazones under Solvent-Free Conditions and Their Potential Application Against Human Triple-Negative Breast Cancer

Some N-tosylhydrazone derivatives were effectively synthesized under solvent-free conditions by using a grinding method at room temperature. The short reaction time, clean and mild process with simple workup and easy purification of the target compounds w

Synthesis of Benzyltributylstannanes by the Reaction of N-Tosylhydrazones with Bu3SnH

An efficient stannylation process with N-tosylhydrazones or directly with carbonyl compounds has been developed. A series of functionalized benzyl- and alkyltributylstannanes can be synthesized in moderate to good yields under transition-metal-free conditions. Tandem transformations involving stannylation/Stille cross-coupling reaction have been carried out without purification of the benzyltributylstannane intermediates to afford a series of diarylmethane derivatives.

Highly stereoselective synthesis of 1-cyanocyclopropane-carboxamides from 3-substituted-2-cyanoacrylamides with N-tosylhydrazones under metal-free conditions

A metal-free cyclopropanation of electron-deficient olefins 3-substituted-2-cyanoacrylamides with N-tosylhydrazones has been successfully developed. This strategy provide a simple route to the synthesis of very valuable 1-cyanocyclopropanecarboxamides wit

Synthesis and antimicrobial evaluation of hydrazones derived from 4-methylbenzenesulfonohydrazide in aqueous medium

A series of biologically active N′-substituted-4-methylbenzenesulfonohydrazide derivatives were synthesized by condensation of 4-methylbenzenesulfonohydrazide and aromatic carbonyl compounds in the presence of polystyrene sulfonic acid in aqueous medium.

Metal-Free Ring-Expansion Reaction of Six-membered Sulfonylimines with Diazomethanes: An Approach toward Seven-Membered Enesulfonamides

A new metal-free, ring-expansion reaction of six-membered N-sulfonylimines with unstable diazomethanes, generated in situ from the N-tosylhydrazones, has been developed. This reaction delivers valuable seven-membered enesulfonamides by a Tiffeneau-Demjanov rearrangement and intramolecular proton transfer tautomerization process. Moreover, this ring-expansion reaction can be carried out in a one-pot fashion and scaled up to the gram scale by using aryl aldehydes, without the need to isolate the N-tosylhydrazone. A diazo thing: The title reaction between cyclic N-sulfonylimines and diazo compounds generated in situ from the N-tosylhydrazones is simple and functional-group tolerant. It thus delivers valuable seven-membered sulfonamides in up to 95 % yield. Moreover, this reaction can be carried out in one-pot starting from the aryl aldehydes, without the need to isolate the N-tosylhydrazone (right).

Palladium-Catalyzed Intermolecular Carbene Insertion Prior to Intramolecular Heck Cyclization: Synthesis of 2-Arylidene-3-aryl-1-indanones

A domino process that converges the migratory insertion of carbene with a Heck reaction has been established as a versatile tool for the synthesis of 2-arylidene-3-aryl-1-indanones from very stable and easily accessible N-tosylhydrazones and 2′-iodochalco