1345876-68-7

Upstream product

• 1250907-72-2 methyl (E)-4-(4-chlorophenyl)but-3-enoate 
• 90797-93-6 4-(4-chloro-phenyl)-but-3-enoic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 36626-29-6 (2-carboxyethyl)triphenylphosphonium chloride 
• 77-78-1 dimethyl sulfate 
• 127404-70-0 (E)-4-(4-chlorophenyl)-3-butenoic acid 

Downstream Products

• 1345876-77-8 (1R,2R)-methyl 1-((E)-4-chlorostyryl)-2-phenylcyclopropanecarboxylate 
• 1416804-21-1 methyl 1-benzyl-2-(4-chlorophenyl)-1,2-dihydroquinoline-4-carboxylate 
• 1589523-11-4 (E)-3-(4-chlorostyryl)-2H-benzo[b][1,4]oxazin-2-one 
• 1589523-15-8 (E)-3-(4-chlorostyryl)-6-methyl-2H-benzo[b][1,4]oxazin-2-one 
• 1589523-19-2 (E)-methyl 3-(4-chlorostyryl)-2-oxo-2H-benzo[b][1,4]oxazine-6-carboxylate 
• 1589522-86-0 methyl 3-(4-chlorobenzyl)-1H-indole-2-carboxylate 
• 1589522-96-2 methyl 5-chloro-3-(4-chlorobenzyl)-1H-indole-2-carboxylate 
• 1589522-88-2 methyl 3-(4-chlorobenzyl)-5-methyl-1H-indole-2-carboxylate 
• 1589522-92-8 methyl 3-(4-chlorobenzyl)-4-methyl-1H-indole-2-carboxylate 
• 79508-09-1 methyl 5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate 

Relevant academic research and scientific papers

Borane Catalyzed Selective Diazo Cross-Coupling Towards Pyrazoles

Decomposition of donor-acceptor diazo compounds leads to the formation of reactive carbene intermediates. These can undergo a wide variety of carbene transfer reactions to yield synthetically useful products. Herein, we report a selective borane catalyzed cyclization reaction from the combination of two different diazo compounds to afford N-substituted pyrazoles. The selective decomposition of the more reactive α-aryl α-diazoester and subsequent reaction with a vinyl diazoacetate produces N-alkylated pyrazoles in a regioselective manner. Catalytic amounts of tris(pentafluorophenyl)borane (10 mol%) were employed to afford the pyrazole products (36 examples) in yields from 59 to 80%. Extensive DFT studies have been undertaken to interpret the mechanism for this reaction which was found to go through two tandem catalytic cycles, both catalyzed by B(C6F5)3.

Intramolecular Cyclization of Vinyldiazoacetates as a Versatile Route to Substituted Pyrazoles

Vinyldiazo compounds undergo a thermal electrocyclization to form pyrazoles in yields of up to 95percent. The reactions are operationally simple, use readily available starting materials, require no intervention of a catalyst, and enable the synthesis of mono-, di- A nd tri-substituted pyrazoles. With the ability to produce highly substituted pyrazoles and the flexibility in installing various types of substituents, this method constitutes a new entry to this valuable heterocyclic scaffold and may be of interest to all branches of the chemical industry.

Synthesis of Allylboranes via Cu(I)-Catalyzed B-H Insertion of Vinyldiazoacetates into Phosphine-Borane Adducts

Cu(I) catalysts enable C-B bond formation via direct insertion of vinyldiazoacetates into B-H bonds of borane-phosphine Lewis adducts to form phosphine-protected allylboranes under mild conditions. The resulting allylborane-phosphine Lewis adducts can be used in the diastereoselective allylation of aldehydes directly without the need for removal of the phosphine. The allylation reaction proceeds with high diastereoselectivity and yields 5,6-disubstituted dihydropyranones after treatment with an appropriate acid.