347187-58-0

Upstream product

• 2158-14-7 4-acetamidobenzenesulfonyl azide 
• 27798-60-3 methyl 2-(2-methoxyphenyl)acetate 

Downstream Products

• 5180-78-9 methyl 2-(2-methoxyphenyl)-2-oxoacetate 
• 1012886-58-6 methyl 2-(2-methoxyphenyl)-2-((4-methoxyphenyl)amino)acetate 

Relevant academic research and scientific papers

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

Copper on charcoal: Cu0nanoparticle catalysed aerobic oxidation of α-diazo esters

By using a charcoal supported nano Cu0catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse the reaction of aryl α-diazo ester with water to form aryl ketoester, 2-aryl-2-hydroxyl acetate ester and 2-aryl acetate ester. In this case, water is split by α-diazo ester, and the diazo group is displaced by the oxygen or hydrogen atom in water. Mechanistic investigation showed that the reaction of α-diazo ester with oxygen proceeds through a radical pathway. In the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, the reaction of α-diazo ester with oxygen is dramatically inhibited. Furthermore, the reaction of α-diazo ester with water is investigated by an isotopic tracer method, and GCMS detection showed that a disproportionation reaction occurred between α-diazo ester and water.

Photoredox Decarboxylative C(sp3)-N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones

Herein we report a metal-free photocatalytic coupling reaction for the synthesis of structurally and functionally diverse N-alkyl hydrazones from α-diazoacetates and N-alkyl hydroxyphthalimide esters. By employing Rose Bengal as a photocatalyst with yellow LEDs irradiation, over 60 N-alkyl hydrazones were synthesized. Fluorescence quenching analysis and deuterium incorporation experiments reveal that Hantzsch ester serves as both an electron donor and proton source for the reaction. This strategy offers a simple retrosynthetic disconnection for conventionally inaccessible C(sp3)-rich N-alkyl hydrazones.

Silica-supported HClO4 promotes catalytic solvent- and metal-free O-H insertion reactions with diazo compounds

Solvent-free O-H insertion reactions in the presence of diazo carbonyl compounds were carried-out in very mild conditions. Unlike the traditional metal-catalysed version, employing rhodium acetate dimer, this method uses eco-friendly silica-supported HClO4 as the catalyst. Only 0.3 mol% of this Br?nsted acid catalyst, that can also be recycled several times, is necessary to guarantee very good yields (up to 97%) in the O-H insertion reactions. Reaction set-up is simple and permitted the preparation of forty-three α-hydroxy and α-alkoxy esters/ketones in just 1 h and at room temperature.

ARTIFICIAL METALLOENZYMES CONTAINING NOBLE METAL-PORPHYRINS

The present invention is drawn to artificial metalloenzymes for use in cyclopropanation reactions, amination and C—H insertion.

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.

Guide to enantioselective dirhodium(II)-catalyzed cyclopropanation with aryldiazoacetates Dedicated to Professor Melanie Sanford in recognition of her receipt of the Tetrahedron Young Investigator Award

Catalytic enantioselective methods for the generation of cyclopropanes have been of long standing pharmaceutical interest. Chiral dirhodium(II) catalysts prove to be an effective means for the generation of diverse cyclopropane libraries. Rh2(R-DOSP)4 is generally the most effective catalyst for asymmetric intermolecular cyclopropanation of methyl aryldiazoacetates with styrene. Rh2(S-PTAD)4 provides high levels of enantioinduction with ortho-substituted aryldiazoacetates. The less-established Rh2(R-BNP)4 plays a complementary role to Rh2(R-DOSP)4 and Rh2(S-PTAD)4 in catalyzing highly enantioselective cyclopropanation of 3-methoxy substituted aryldiazoacetates. Substitution on the styrene has only moderate influence on the asymmetric induction of the cyclopropanation.

Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary r,r-heterodiaryl carboxylic esters

A rhodium-catalyzed one-pot three-component coupling reaction was developed for the synthesis of quaternary α,α-heterodiaryl carboxylic esters. This reaction involves cross-coupling of the arylrhodium(I) complexes with R-aryldiazoacetates to form oxa-π-al

Ruthenium catalyzed directing group-free C2-selective carbenoid functionalization of indoles by α-aryldiazoesters

[Chemical equation presented] A directing group-free approach for C2-selective carbenoid functionalization of NH-indoles is presented. Using [RuCl2(p-cymene)]2 as catalyst and α-aryldiazoesters as carbenoid source, 2-alkylated indoles were obtained in up to 96% isolated yield. Similarly, a regioselective carbenoid functionalization of NH-pyrroles was also achieved.

Palladium-catalyzed cross coupling reaction of benzyl bromides with diazoesters for stereoselective synthesis of (E)-α,β-diarylacrylates

(Chemical Equation Presented) A Pd-catalyzed cross-coupling reaction of benzyl bromides with α-aryldiazoesters is described, and E-α,β-diarylacrylates were obtained in good yields and excellent E-to-Z selectivity (>20:1).