22979-35-7

Upstream product

• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 24461-61-8 phenylglycine methyl ester 
• 101-41-7 benzeneacetic acid methyl ester 
• 19883-41-1 D-phenylglycine methyl ester hydrochloride 
• 2158-14-7 4-acetamidobenzenesulfonyl azide 
• 941-55-9 4-toluenesulfonyl azide 
• 122-79-2 Phenyl acetate 
• 18793-81-2 methyl 2-phenyl-2-(2-tosylhydrazono)acetate 
• 71-43-2 benzene 
• 16648-44-5 methyl α-acetylphenylacetate 
• 103-82-2 phenylacetic acid 
• 54108-62-2 3-Oxo-2,3-diphenylpropenoic acid methyl ester 
• 121-44-8 triethylamine 
• 1334313-47-1 (Z)-methyl 2-phenyl-2-(2-tosylhydrazono)acetate 

Downstream Products

• 72410-80-1 3-Chloro-1-phenyl-cyclopent-3-enecarboxylic acid methyl ester 
• 42332-99-0 methyl rel-(1R,2R)-2-ethyl-1,2-diphenylcyclopropanecarboxylate 
• 42400-68-0 (+/-)-methyl 1β,2β-diphenylcyclopropane-1α-carboxylate 
• 13314-91-5 dimethyl stilbene-1,2-dicarboxylate 
• 82555-62-2 methyl 2-methyl-1-phenyl-3-(trimethylsilyl)-2-cyclopropene-1-carboxylate 
• 127218-69-3 3-cyano-3-dimethylamino-2-phenylpropionic acid methyl ester 
• 127590-13-0 1-Phenyl-2-(trimethylsiloxy)cyclopropancarbonsaeure-methylester (trans) 
• 127218-68-2 3-Dimethylamino-4-oxo-2-phenyl-pentanoic acid methyl ester 
• 127218-67-1 2-Dimethylamino-3-phenyl-succinic acid dimethyl ester 
• 82555-63-3 methyl 2-tert-butyl-1-phenyl-3-(trimethylsilyl)-2-cyclopropene-1-carboxylate 
• 127218-64-8 1-methoxycarbonyl-2-diethylamino-1-phenylpropane 
• 103615-36-7 5-methoxy-2-methyl-4-phenyl-1,3-oxazole 
• 76369-03-4 methyl α-isopropoxy-α-phenylacetate 
• 134306-43-7 methyl 2-(((benzyloxy)carbonyl)amino)-2-phenylacetate 

Relevant academic research and scientific papers

Efficient synthesis of chiral cyclic acetals by metal and Bronsted acid co-catalyzed enantioselective four-component cascade reactions

Four-component Mannich reactions subsequently followed by an intramolecular oxo-Michael addition were developed to efficiently produce chiral cyclic acetals with high diastereoselectivity and enantioselectivity. The Royal Society of Chemistry.

Atom-economical access to highly substituted indenes and furan-2-ones via tandem reaction of diazo compounds and propargyl alcohols

A facile synthesis of highly substituted as well as conjugated indene/furanone systems via a BF3·OEt2 catalyzed tandem reaction of α-diazo-esters/-amides and propargyl alcohols has been demonstrated under mild conditions. This method

Palladium-Catalyzed Migratory Insertion of Carbenes and C-C Cleavage of Cycloalkanecarboxamides

A palladium catalyzed reaction of cycloalkanecarboxamides and diazomalonates or bis(phenylsulfonyl)diazomethane has been developed. The reaction proceeds via carbene migratory insertion and cascade C-C cleavage pathways. Cycloalkanecarboxamides with four to seven membered rings are applicable in the transformation. A series of ring opening products were prepared with moderate yields. The finding provides valuable clues for the development of new reactions involving carbene migratory insertion and the cleavage of unstrained C(sp3)-C(sp3) bonds.

Synthesis of Functionalized Silsesquioxane Nanomaterials by Rhodium-Catalyzed Carbene Insertion into Si?H Bonds

We report carbene insertion into Si?H bonds of polyhedral oligomeric silsesquioxanes (POSS) for the synthesis of highly functionalized siloxane nanomaterials. Dirhodium(II) carboxylates catalyze insertion of aryl-diazoacetates as carbene precursors to afford POSS structures containing both ester and aryl groups as orthogonal functional handles for further derivatization of POSS materials. Four diverse and structurally varied silsesquioxane core scaffolds with one, three, or eight Si?H bonds were evaluated with diazo reactants to produce a total of 20 new POSS compounds. Novel diazo compounds containing a fluorinated octyl group and boron-dipyrromethene (BODIPY) chromophore demonstrate the use of highly functionalized substrates. Transformations of aryl(ester)-functionalized POSS compounds derived from this method are demonstrated, including ester hydrolysis and Suzuki–Miyaura cross-coupling.

Blue LED Induced Manganese (I) Catalysed Direct C2?H Activation of Pyrroles with Aryl Diazoesters

Herein, we have reported a blue LED mediated manganese pentacarbonyl bromide catalysed incorporation of carbene moieties from aryl diazoesters onto 1H-pyrroles via their selective C2?H activation. A manganese metal-carbene has been identified as the active catalyst to facilitate the reaction. Eighteen mono substituted pyrrole derivatives were isolated in good to excellent yields (67→82%) and the disubstituted products were also formed in minor quantities (5 to 8%). HPLC based kinetics study enabled optimization of the reaction. Control experiments, FT-IR, NMR and GC-MS based characterization elucidated the putative reaction mechanism. (Figure presented.).

Catalyst-free, scalable heterocyclic flow photocyclopropanation

Industrial process development is driven by several factors, including safety, cost, robustness and environmental aspects. However, attempts to establish aryl diazo esters-which are highly valued in academic research for their reactivity as carbene precur

Copper-Catalyzed 1,1-Alkylmonofluoroalkylation of Terminal Alkynes with Diazo Compounds and 2-Fluoro-1,3-dicarbonyl Compounds: Access toward (E)-β-Monofluoroalkyl-β,γ-unsaturated Esters or Ketones

An efficient copper-catalyzed three-component 1,1-alkylmonofluoroalkylation of terminal alkynes, diazo compounds, and 2-fluoro-1,3-dicarbonyl compounds for the synthesis of (E)-β-monofluoroalkyl-β,γ-unsaturated esters or ketones has been developed. The methodology features a broad substrate scope, an inexpensive and easily available catalytic system, and excellent selectivity with good yields. The mechanism of the tandem Cu-catalyzed cross-coupling and nucleophilic addition of allenes has been investigated.

Borane catalysed cyclopropenation of arylacetylenes

Triarylboranes have gained substantial attention as catalysts for C-C bond forming reactions due to their remarkable catalytic activities. Herein, we report B(C6F5)3catalysed cyclopropenation of a wide variety of arylacetylenes using donor-acceptor diazoesters. A mild reaction protocol has been developed for the synthesis of functionalised cyclopropenes (33 examples) in good to excellent yields.

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.

α-Xanthylmethyl Ketones from α-Diazo ketones

A simple and efficient method to obtain α-xanthylmethyl ketones from α-diazo ketones is described. The reaction proceeds through a protonation/nucleophilic substitution sequence in the presence of p -toluenesulfonic acid and potassium ethyl xanthogenate as the nucleophile. As α-diazo ketones can be readily synthesized from ubiquitous carboxylic acids, a broad variety of xanthates can be obtained, including examples from naturally occurring substrates.