19277-54-4

Upstream product

• 52372-80-2 (4-chlorobenzylidene)hydrazine 
• 104-88-1 4-chlorobenzaldehyde 
• 6655-32-9 N'-(4-chlorobenzylidene)-2-nitrobenzenesulfonohydrazide 

Downstream Products

• 87-87-6 2,3,5,6-tetrachlorobenzene-1,4-diol 
• 104-88-1 4-chlorobenzaldehyde 
• 120106-66-3 4,5-bis(4-chlorophenyl)-2H-1,2,3-triazole 
• 1195-44-4 4-chlorobenzyl methyl ether 
• 98446-71-0 1-Chloro-4-((2R,3S)-2-isopropyl-3-methyl-cyclopropyl)-benzene 
• 65354-61-2 2-(p-Chlorophenyl)-3,3-dimethylmethylenecyclopropane 
• 57765-59-0 2-(p-Chlorophenyl)isopropylidenecyclopropane 
• 104183-69-9 4-(p-chlorophenyl)-3-(dicyanomethyl)quinolin-2-one 
• 70405-49-1 C₁₆H₁₇ClN₄O₂ 
• 70515-51-4 C₁₈H₁₉ClN₄O₄ 
• 70405-48-0 C₁₄H₁₃ClN₄ 
• 2510-74-9 (E)-1,2-di(4-chlorophenyl)ethene 
• 2510-74-9 cis-4,4'-dichlorostilbene 
• 5121-74-4 4,4'-dichlorostylbene 

Relevant academic research and scientific papers

Preparation method of mild diazomethane derivative

The invention discloses a preparation method of a mild diazomethane derivative. The preparation method comprises that EWG-substituted benzene sulfonyl chloride and hydrazine hydrate undergo a reaction to produce EWG-substituted benzene sulfonyl chloride, the EWG-substituted benzene sulfonyl chloride and aldehyde or ketone undergo a reaction to produce EWG-substituted benzenesulfonylhydrazone, and the EWG-substituted benzenesulfonylhydrazone, a base and an organic solvent are mixed and undergo a replacement reaction to produce a diazomethane derivative. The diazomethane derivative is not separated and purified and is further used for a tension small ring synthesis reaction and an insertion reaction. The benzene ring of benzenesulfonylhydrazone is introduced with an electron-withdrawing group EWG, and through electron effects and steric hindrance effects, the benzenesulfonyl group on the benzenesulfonylhydrazone is easily separated so that a diazomethane derivative is produced under very mild conditions and especially at the room temperature.

Silver-Catalyzed [2+1] Cyclopropenation of Alkynes with Unstable Diazoalkanes: N-Nosylhydrazones as Room-Temperature Decomposable Diazo Surrogates

The [2+1] cycloaddition of alkynes with diazo compounds represents one of the most powerful and reliable methods for the construction of cyclopropenes. However, it remains a formidable challenge to accomplish the cyclopropenation of alkynes with non-stabilized diazoalkanes, owing to the fact that such compounds are unstable and prone to detonation. Herein, we report a general silver-catalyzed cyclopropenation reaction of alkynes with unstable diazoalkanes, by for the first time the discovery and application of N-nosylhydrazones as room-temperature decomposiable diazo surrogates. This method allows for the efficient assembly a wide variety of cyclopropene derivatives that are otherwise difficult to access by conventional methods.

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines

We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10–20 minutes with high enantioselectivity (89–98 % de/ee), moderate yields and a wide functional group tolerance.

A Versatile Room-Temperature Route to Di- and Trisubstituted Allenes Using Flow-Generated Diazo Compounds

A copper-catalyzed coupling reaction between flow-generated unstabilized diazo compounds and terminal alkynes provides di- and trisubstituted allenes. This extremely mild and rapid transformation is highly tolerant of several functional groups. Well tolerated: A mild copper-catalyzed coupling reaction between unstabilized diazo compounds (generated in flow) and terminal alkynes is reported. The method provides di- and trisubstituted allenes with high functional-group tolerance.