19816-85-4

Usage

Uses

Desoxybenzoin p-toluenesulfonylhydrazone is used as the reagent.

InChI:InChI=1/C22H22N2O2S/c1-18-12-14-22(15-13-18)27(25,26)24-23-21(16-19-8-4-2-5-9-19)17-20-10-6-3-7-11-20/h2-15,24H,16-17H2,1H3

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 501-65-5 diphenyl acetylene 

Downstream Products

• 451-40-1 phenyl benzyl ketone 
• 621-06-7 2,N-diphenylacetamide 
• 588-59-0 stilbene 
• 3314-83-8 1,2,3,4-tetraphenyl-2-butene 
• 65200-71-7 4,5-diphenyl-[1,2,3]thiadiazole 1,1,3-trioxide 
• 1262210-34-3 (Z)-(1-(2-chloro-4-methoxyphenyl)ethene-1,2-diyl)dibenzene 
• 1985-77-9 (Z)-(1-(o-tolyl)ethene-1,2-diyl)dibenzene 
• 1233-23-4 (Z)-1-(4-methoxyphenyl)-1,2-diphenylethylene 
• 98901-14-5 N-tert-butyl-2,3-diphenylpropanamide 
• 182162-88-5 C₂₂H₂₀ 
• 92133-95-4 1-benzyl-3,5-diphenyl-1H-pyrazole 

Relevant academic research and scientific papers

Synthetic Routes for Heteroatom-Containing Alkylated/Arylated Polycyclic Aromatic Hydrocarbons

Synthetic routes for heteroatom-containing polycyclic aromatic hydrocarbons (H-PAHs) with alkyl and aryl substitution are demonstrated. Three H-PAHs, including heteroatom-containing rubicenes (H-rubicenes), angular-benzothiophenes (ABTs), and indenothioph

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.

I2-Promoted [4 + 2] cycloaddition of: In situ generated azoalkenes with enaminones: Facile and efficient synthesis of 1,4-dihydropyridazines and pyridazines

A facile and efficient strategy for the synthesis of 1,4-dihydropyridazines and pyridazines through I2-promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones has been developed. The switch in selectivity is attributed to the judici

Pd-Catalyzed Heck-Type Reaction: Synthesizing Highly Diastereoselective and Multiple Aryl-Substituted P-Ligands

In this work, an efficient palladium-catalyzed Heck-type reaction was successfully used to synthesize a wide range of monoaryl-or diaryl-substituted P-ligands with excellent yields and diastereoselectivity (up to 98% yield, dr >20:1). The preliminary mechanistic studies demonstrated that it possibly underwent a cationic Heck reaction that was assisted by silver salt, and it revealed the significant role of P(O)Ar2 for excellent yields and diastereoselectivity.

Pd-Catalyzed Tandem Coupling Reaction of 2-gem-Dibromovinylanilines and N-Tosylhydrazones to Construct 2-(1-phenylvinyl)-indoles

A novel palladium(0)-catalyzed intermolecular coupling reaction of 2-gem-dibromovinylanilines and N-tosylhydrazones was reported to construct 2-(1-phenylvinyl)-indoles efficiently. The indole bearing 1, 1-disubstituted alkenes were obtained in one step wi

Hydrohydrazination of Arylalkynes Catalyzed by an Expanded Ring N-Heterocyclic Carbene (er-NHC) Gold Complex under Solvent-Free Conditions

[(THD-Dipp)AuOTf], supported by the strongly electron donating, sterically bulky THD-Dipp (1,3-bis(2,6-diisopropylphenyl)hexahydro-2H-1,3-diazepine-2-ylidene) seven-membered N-heterocyclic carbene ligand, efficiently promotes intermolecular addition of Ts- and Boc-hydrazine to arylalkynes under solvent-free conditions.

Pd-Catalyzed Highly Regio- and Stereoselective Formation of C-C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes

A highly regio- and stereoselective C-C double bond formation reaction via Pd-catalyzed Heck-type cascade process with N-tosylhydrazones has been developed. Various N-tosylhydrazones derived from both ketones and aldehydes are found to be efficient substrates to provide di- and trisubstituted olefins with high regio- and stereoselectivity. Furthermore, this reaction has a good functional group tolerance and different benzofuran-, dihydrobenzofuran-, and indoline-containing alkene products were obtained with high selectivity.

Copper-catalyzed radical reaction of N -tosylhydrazones: Stereoselective synthesis of (E)-vinyl sulfones

A new chemistry of hydrazines that is a copper-catalyzed radical reaction to synthesize vinyl sulfones from readily available N-tosylhydrazones has been described. The protocol provides a novel strategy for the synthesis of various vinyl sulfones including α, β-disubstituted ones and terminal ones. The advantages of the transformation include excellent E stereoselectivity, broad substrate scope, low cost of reagents, and convenient operation. A novel and efficient one-pot synthesis of alkynes from N-tosylhydrazones has been achieved. The studies provide important complementary approaches for the syntheses of vinyl sulfones and alkynes.

Regioselective Synthesis of Vinyl Halides, Vinyl Sulfones, and Alkynes: A Tandem Intermolecular Nucleophilic and Electrophilic Vinylation of Tosylhydrazones

A diazo species is trapped in an intermolecular fashion by two independent ion species in tandem at the carbene center to install an electrophile and a nucleophile on the same carbon. This metal-free concept, which is unprecedented, has been illustrated by regioselective synthesis of a variety of vinyl halides, vinyl sulfones, and alkyne derivatives. (Chemical Equation Presented).

Tandem one-pot palladium-catalyzed coupling of hydrazones, haloindoles, and amines: Synthesis of amino-N-vinylindoles and their effect on human colon carcinoma cells

The synthesis of amino-substituted N-vinylazoles was achieved by a new palladium-assisted tandem catalytic reaction involving N-tosylhydrazones, halo-substituted azoles, and amines. Accordingly, two Csp2-N bonds were formed through two mechanistically distinct reactions using a single PdII/Pd0 catalyst system in a one-pot fashion. This work paves the way for the design of biological relevant compounds in an amino-substituted N-vinylindole series. Among several polyoxygenated derivatives evaluated, compounds 5e and 5u were found to exhibit good antiproliferative activity.