219564-79-1

Upstream product

• 941-55-9 4-toluenesulfonyl azide 
• 34837-84-8 4-fluorobenzeneacetic acid methyl ester 
• 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 

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.

2-azabicyclo [3.2.0] compound as well as synthesis method and application

The invention discloses a 2-azabicyclo [3.2.0] compound as well as a synthesis method and an application. The 2-azabicyclo [3.2.0] compound comprises a compound with a structure as shown in a formula I and pharmaceutically acceptable salts thereof, wherein R is a substituted or unsubstituted benzene ring, a C1-8 aliphatic group or trifluoromethyl, R1 and R2 are respectively a substituted or unsubstituted benzene ring, a hydrogen atom or a C1-8 aliphatic group, R3 is a substituted or unsubstituted benzene ring, a hydrogen atom, a C1-8 aliphatic group or a heterocyclic substituent, R4 is a heterocyclic substituent or a substituted or unsubstituted benzene ring, R5 is a C1-8 fatty group, a benzyl group or -COOR6, and R6 is a C1-4 fatty group or a benzyl group. The invention belongs to the technical field of pharmaceutical chemicals, and after the prepared 2-azabicyclo [3.2.0] compound acts on an animal body, anti-sedation and anti-hypnosis effects can be achieved by adjusting the intracerebral level of histamine.

Visible Light-Promoted Sulfoxonium Ylides Synthesis from Aryl Diazoacetates and Sulfoxides

A visible light-promoted reaction of donor/acceptor diazoalkanes with sulfoxides towards the synthesis of synthetically useful sulfoxonium ylides was reported. The reaction occurred under sole visible light irradiation without the need of any transition-metals or additives, affording the corresponding sulfoxonium ylides in moderate to good yields. The success of late-stage modification of natural isolates or drug candidates, scale-up reaction and transformation of sulfoxonium ylides to other useful molecules further rendered the approach valuable.

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.

B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes

Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of 10 mol% of B(C6F5)3. These reactions provide N1-alkylated benzotriazoles in good to excellent yields and this protocol is successfully adapted to gram-scale syntheses as well as a derivative with antimicrobial activity.

Insertion of Diazo Esters into C-F Bonds toward Diastereoselective One-Carbon Elongation of Benzylic Fluorides: Unprecedented BF3Catalysis with C-F Bond Cleavage and Re-formation

Selective transformation of C-F bonds remains a significant goal in organic chemistry, but C-F insertion of a one-carbon-atom unit has never been established. Herein we report the BF3-catalyzed formal insertion of diazo esters as one-carbon-atom sources into C-F bonds to accomplish one-carbon elongation of benzylic fluorides. A DFT calculation study revealed that the BF3 catalyst could contribute to both C-F bond cleavage and re-formation. This elongation provided α-fluoro-α,β-diaryl esters with a high level of diastereoselectivity. Various benzylic fluorides and diazo esters were applicable. The synthetic utility of this method was demonstrated by the synthesis of a fluoro analogue of a compound that is used as a transient receptor and potential canonical channel inhibitor.

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).