239094-37-2

Upstream product

• 17145-48-1 ethyl 2-diazo-2-(trimethylsilyl)acetate 
• 555-16-8 4-nitrobenzaldehdye 
• 623-73-4 diazoacetic acid ethyl ester 
• 55718-77-9 ethyl lithiodiazoacetate 

Downstream Products

• 239094-49-6 C₁₉H₁₈N₄O₈S 
• 75414-82-3 ethyl 2-diazo-3-(4-nitrophenyl)-3-oxopropanoate 
• 1591911-98-6 C₂₂H₁₉FeN₃O₆ 

Relevant academic research and scientific papers

A Conjugate Addition Approach to Diazo-Containing Scaffolds with β Quaternary Centers

Structurally complex diazo-containing scaffolds are formed by conjugate addition to vinyl diazonium salts. The electrophile, a little studied α-diazonium-α,β-unsaturated carbonyl compound, is formed at low temperature under mild conditions by treating β-h

Highly efficient and chemoselective direct aldol reaction of acyldiazomethane with aldehydes promoted by MgI2 etherate

Direct aldol condensation of various aromatic, heteroaromatic, α,β-unsaturated aldehydes and aliphatic aldehydes with acyldiazomethane was realized using MgI2 etherate (MgI2·(Et2O)n) as a promoter in the presence of diisopropyl amine (DIPEA) in excellent yields in a short time under mild conditions with high chemoselectivity. Iodide counterion, and a non-coordinating less ploar reaction media (i.e., CH2Cl2) are among the critical factors for this unique reactivity.

An efficient and convenient aldol addition of acyldiazomethane with aldehydes promoted by MgI2 etherate

The aldol addition of acyldiazomethane with aromatic aldehydes, vinyl aldehyde and aliphatic aldehydes was carried out efficiently in the presence of MgI2 etherate and iPr2EtN (DIPEA) using untreated reagent-grade CH2Cl2 under atmospheric conditions in good to excellent yields. Iodide counterion and a non-coordinating reaction media (i.e. CH2Cl2) are among the critical factors for the unique reactivity of this reaction system.

Deep eutectic solvent (DES) as dual solvent/catalyst for synthesis of α-diazocarbonyl compounds using aldol-type coupling

Deep eutectic solvent (DES) was employed as dual solvent/catalyst in the green synthesis of α-diazocarbonyl compounds using aldol-type coupling. α-Diazocarbonyl compounds are important synthetic intermediates with useful application for synthesis of amino alcohols and acids and many natural products. Moreover, the method is environmentally friendly because of avoidance of toxic solvents or hazardous catalysts.

An efficient aldol-type reaction of ethyl diazoacetate with aldehydes promoted by MgI2 etherate

The first example of the preparation of α-diazo-β-hydroxy esters by the aldol-type condensation of aldehydes with ethyl diazoacetate using Et3N as base in the presence of magnesium iodide etherate [MgI2.(Et2O)n] has been achieved in good to excellent yields at room temperature in CH2Cl2 in 15-30 min.

Rh2(OAc)4-catalyzed 2,3-migration of β-ferrocenecarboxyl α-diazocarbonyl compounds: An efficient synthesis of ferrocene-containing α,β-unsaturated esters

A series of β-ferrocenecarboxyl α-diazocarbonyl compounds were prepared by the reaction of ferrocenoyl chloride with β-hydroxyl α-diazocarbonyl compounds in the presence of pyridine. The diazo decomposition of these ferrocene-containing diazocarbonyl compounds with Rh 2(OAc)4 resulted in 2,3-ferrocenecarboxyl migration to give ferrocene-containing α,β-unsaturated esters in high yields.

Pyrrolidine-catalyzed condensation of ethyl diazoacetate to aldehydes in water

A simple and convenient protocol for the synthesis of-diazo carbonyl compounds from the condensation of ethyl diazoacetate to aldehydes in water was developed using pyrrolidine as a catalyst. Copyright

A mild, efficient method for the oxidation of α-diazo-β-hydroxyesters to α-diazo-β-ketoesters

A wide variety of α-diazo-β-ketoesters can be prepared in good overall yields via a two-step sequence involving addition of ethyl lithiodiazoacetate to aliphatic, aromatic, and conjugated aldehydes followed by mild oxidation with the Dess-Martin periodina

Silica-supported tetramethylguanidine: An efficient solid base for aldol-type coupling of aldehydes with ethyl diazoacetate

Silica-supported tetramethylguanidine catalyst was prepared and effectively used in the aldol-type coupling of aldehydes with ethyl diazoacetate to afford the corresponding α-diazo-β-hydroxy esters in good to excellent yields. The catalyst was quantitatively recovered from the reaction by a simple filtration and reused for a number of cycles with almost consistent activity. Georg Thieme Verlag Stuttgart.

Catalysis in water: Aldol-type reaction of aldehydes and imines with ethyl diazoacetate catalyzed by highly basic magnesium/lanthanum mixed oxide

Magnesium/lanthanum mixed oxide is an effective heterogeneous catalyst for aldol-type condensation of aldehydes and imines with ethyl diazoacetate (EDA) at room temperature in water to afford corresponding β-hydroxy-α-diazo carbonyl compounds and β-amino-α-diazo carbonyl compounds in good yields. The catalyst is recovered and reused for several cycles with consistent activity.