234084-69-6

Upstream product

• 36626-29-6 (2-carboxyethyl)triphenylphosphonium chloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 77-78-1 dimethyl sulfate 
• 91142-97-1 4-(p-methoxyphenyl)-3-butenoic acid 
• 127404-73-3 (3E)-4-(4-methoxyphenyl)but-3-enoic acid 
• 130028-18-1 (E)-4-(4-Methoxy-phenyl)-but-3-enoic acid methyl ester 

Downstream Products

• 1204478-51-2 (3R,3aR,8bS)-methyl 3-(4-methoxyphenyl)-3a,4-dimethyl-3,3a,4,8b-tetrahydrocyclopenta[b]indole-1-carboxylate 
• 1285704-98-4 4-ethyl 1-methyl 2-((E)-4-methoxystyryl)fumarate 
• 192701-83-0 methyl 5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate 
• 1589523-05-6 methyl 4-(4-methoxyphenyl)-7-nitroquinoline-2-carboxylate 
• 868234-57-5 (E)-3-(4-methoxystyryl)-2H-benzo[b][1,4]oxazin-2-one 
• 1454283-85-2 5-benzyl 2-methyl 4-(4-methoxyphenyl)-6-methylpyridine-2,5-dicarboxylate 

Relevant academic research and scientific papers

Tris(pentafluorophenyl)borane-Catalyzed Carbenium Ion Generation and Autocatalytic Pyrazole Synthesis—A Computational and Experimental Study

In recent years, metal-free organic synthesis using triarylboranes as catalysts has become a prevalent research area. Herein we report a comprehensive computational and experimental study for the highly selective synthesis of N-substituted pyrazoles throu

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.

Synthesis of [18 F]-γ-Fluoro-α,β-unsaturated Esters and Ketones via Vinylogous 18 F-Fluorination of α-Diazoacetates with [18 F]AgF

This communication reports a method for the vinylogous radiofluorination of α-diazoacetates to generate [18 F]-γ-fluoro-α,β-unsaturated esters and ketones in moderate to good radiochemical yields. The method uses no-carrier-added [18 F]AgF and is compatible with aromatic and non-aromatic substrates and a number of different functional groups. The labeling method is showcased in the synthesis of a fluorinated cholest-5-en-3-one derivative as well as a difluorinated product pertinent to drug discovery.

Synthesis of pyridines by carbenoid-mediated ring opening of 2H-azirines

Roaming the range: The title reaction tolerates a wide range of substituents on the resulting pyridine ring using mild reaction conditions (see scheme; esp=α,α,α′,α′-tetramethyl-1,3- benzenedipropionic acid). The formation of the key intermediate is catal

Rhodium(II)-catalyzed cross-coupling of diazo compounds

Nothing left to chance: A convenient protocol for selective cross-coupling of diazo compounds for the convergent synthesis of alkenes was developed (see scheme; EDG=aryl, heteroaryl, vinyl; R=O-alkyl, aryl). The selectivity control elements were identifie

4-Substituted and 7-substituted indoles, benzofurans, benzothiophenes, benzimidazoles, benzoxazoles, and benzothiazoles and methods for making same

Disclosed are 4-substituted and 7-substituted indoles, benzofurans, benzothiophenes, benzimidazoles, benzoxazoles, and benzothiazoles. Also disclosed are methods for making 4-substituted and 7-substituted indoles, benzofurans, benzothiophenes, benzimidazo

Direct synthesis of methyl 2-diazo-4-aryl-3-butenoates and their application to the enantioselective synthesis of 4-aryl-4-(1-naphthyl)-2-butenoates

An improved one-flask synthesis of various methyl 2-diazo-4-aryl and 4-heteroaryl-3-butenoates, precursors to donor/acceptor substituted carbenoids, is described. Their Rh2(S-DOSP)4 catalyzed reaction with 1-acetoxy-3,4-dihydronaphth

Catalytic asymmetric synthesis of diarylacetates and 4,4-diarylbutanoates. A formal asymmetric synthesis of (+)-sertraline

(equation presented) The intermolecular C-H insertion chemistry of phenyldiazoacetates catalyzed by dirhodium tetrakis((S)-N-(dodecylbenzenesulfonyl)prolinate) (Rh2(S-DOSP)4) can be effectively carried out on cyclohexadienes, leading to the asymmetric synthesis of diarylacetates. The reaction of vinyldiazoacetates with cyclohexadienes results in an unprecedented carbenoid reaction that is formally a combined C-H insertion/Cope rearrangement. The synthetic utility of this novel transformation was demonstrated by its utilization in a formal asymmetric synthesis of (+)-sertraline.