219564-79-1

Upstream product

• 34837-84-8 4-fluorobenzeneacetic acid methyl ester 
• 941-55-9 4-toluenesulfonyl azide 
• 405-50-5 p-Fluorophenylacetic acid 
• 156276-23-2 methyl (p-fluorobenzoyl)formate 

Downstream Products

• 156276-23-2 methyl (p-fluorobenzoyl)formate 
• 1000702-71-5 C₁₈H₂₅FO₃Si 
• 32222-46-1 (4-fluoro-phenyl)-hydroxy-acetic acid methyl ester 
• 63096-35-5 (4-fluoro-phenyl)-hydroxy-acetic acid methyl ester 
• 1190830-61-5 methyl [2-cyano-2-(4-fluorophenyl)]acetate 
• 1206707-16-5 methyl 2-(4-fluorophenyl)-2-(1H-indol-2-yl)acetate 
• 1228468-17-4 methyl 1-(4-fluorophenyl)-2-(2-methoxyethoxymethoxymethyl)cycloprop-2-enecarboxylate 
• 1301262-72-5 (5R,11S,14S)-methyl 14-(4-fluorophenyl)-2,8-dimethyl-6,12-dihydro-5,11-ethanodibenzo[b,f][1,5]diazocine-14-carboxylate 
• 1291088-14-6 methyl 3-(benzyloxycarbonylamino)-2-(4-fluorophenyl)-2,3-diphenylpropanoate 
• 1437744-55-2 (E)-methyl 2-(2-(dimethoxyphosphoryl)hydrazono)-2-(4-fluorophenyl)acetate 

Relevant academic research and scientific papers

Oxime Ether Synthesis through O-H Functionalization of Oximes with Diazo Esters under Blue LED Irradiation

A green and sustainable oxime ether formation method via the visible-light-promoted O-H functionalization of oximes with diazo esters is described. The reaction occurs under very mild conditions (catalyst- and additive-free) with a high yield and a high functional group tolerance. When the reaction was performed with a cyclic ether as the solvent (e.g., THF, 1,4-dioxane, tetrahydropyran, ect.), an interesting photochemical three-component reaction product was obtained in good yields.

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.

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.

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.

Tropylium-Catalyzed O-H Insertion Reactions of Diazoalkanes with Carboxylic Acids

Herein, we describe the application of a nonbenzenoid aromatic carbocation, namely tropylium, as an organic Lewis acid catalyst in O-H functionalization reactions of diazoalkanes with benzoic acids. The newly developed protocol is applicable to a wide range of diazoalkane and carboxylic acid substrates with excellent efficiency (43 examples, up to 99% yield).

Dirhodium(II)/Xantphos-Catalyzed Relay Carbene Insertion and Allylic Alkylation Process: Reaction Development and Mechanistic Insights

Although dirhodium-catalyzed multicomponent reactions of diazo compounds, nucleophiles and electrophiles have achieved great advance in organic synthesis, the introduction of allylic moiety as the third component via allylic metal intermediate remains a formidable challenge in this area. Herein, an attractive three-component reaction of readily accessible amines, diazo compounds, and allylic compounds enabled by a novel dirhodium(II)/Xantphos catalysis is disclosed, affording various architecturally complex and functionally diverse α-quaternary α-amino acid derivatives in good yields with high atom and step economy. Mechanistic studies indicate that the transformation is achieved through a relay dirhodium(II)-catalyzed carbene insertion and allylic alkylation process, in which the catalytic properties of dirhodium are effectively modified by the coordination with Xantphos, leading to good activity in the catalytic allylic alkylation process.

B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids

A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.

Visible-Light-Promoted Polysubstituted Olefins Synthesis Involving Sulfur Ylides as Carbene Trapping Reagents

A blue-light-emitting diode (LED) promoted coupling of aryl diazoacetates with sulfur ylides is described. This protocol features mild conditions, good functional group tolerance, and broad substrate scope for both aryl diazoacetates with sulfur ylides. Under optimal reaction conditions, a wide range of trisubstituted olefins is obtained in moderate to good yield, which can be further transferred to other biologically important heterocycles after a two-step simple operation.

Visible-light-promoted selective: O -alkylation of 2-pyridones with α-aryldiazoacetates

A visible-light-promoted O-H insertion reaction between 2-pyridones and α-aryldiazoacetates has been developed. Upon visible light irradiation, the reaction proceeds smoothly under mild and catalyst-free conditions. A wide scope of 2-pyridones and α-aryldiazoacetates are well tolerated, and various O-alkylated 2-pyridones are obtained with perfect selectivity and good functional group tolerance. A photoinduced radical process is probably responsible for the excellent selectivity. This journal is

Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation

We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that the reaction occurs under sole visible light irradiation without the need for exogenous photoredox catalysts. More significantly, a reasonable reaction mechanism was proposed on the basis of the control experiments and density functional theory calculation results.