239094-36-1

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 1122-91-4 4-bromo-benzaldehyde 
• 17145-48-1 ethyl 2-diazo-2-(trimethylsilyl)acetate 

Downstream Products

• 1591911-92-0 C₂₂H₁₉BrFeN₂O₄ 
• 26510-95-2 ethyl 4-Bromobenzoylacetate 

Relevant academic research and scientific papers

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.

Safe generation and direct use of diazoesters in flow chemistry

A safe and fast method for the production of β-hydroxy-α- diazoesters in continuous flow technology is described. The synthesis involves the formation of ethyl diazoacetate in situ and the addition to several aldehydes in a two-step continuous flow microreactor setup. Rhodium acetate catalyzes a subsequent 1,2-hydride shift to give access to β-keto esters in a three-step sequence. Georg Thieme Verlag Stuttgart · New York.

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.

Tert-BuOK-Catalyzed condensation of ethyl diazoacetate to aldehydes and palladium-catalyzed 1,2-hydrogen migration for the synthesis of β-ketoesters under solvent-free conditions

A mild and convenient method for the condensation of ethyl diazoacetate (EDA) with aldehydes catalyzed by tert-BuOK under solvent-free conditions was developed. The corresponding α-diazo-β-hydroxy esters were further converted into β-ketoesters through palladium-catalyzed 1,2-hydrogen migration under neat conditions. The two-step transformation exemplifies a simple method for the efficient and green synthesis of β-ketoesters. The Royal Society of Chemistry 2013.

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

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.

DBU-catalyzed condensation of acyldiazomethanes to aldehydes in water and a new approach to ethyl β-hydroxy α-arylacrylates

DBU-catalyzed condensation of ethyl diazoacetate (EDA) with aldehydes in pure water afforded corresponding β-hydroxy α-diazo carbonyl compounds. The β-hydroxy group of the products was further converted into β-siloxy group. The Rh(II)-catalyzed reaction of the β-aryl β-siloxy α-diazo carbonyl compounds gave 1,2-aryl shift products predominantly. The three-step transformation constitutes an efficient synthesis of ethyl β-hydroxy α-arylacrylates.

Synthesis of α-diazo-β-hydroxy esters using nanocrystalline MgO

Nanocrystalline magnesium oxide (NAP-MgO) has been found to be an effective heterogeneous, solid base catalyst for the direct aldol type reaction of ethyl diazoacetate and various aldehydes to afford the corresponding α-diazo-β-hydroxy esters in excellent yields with high selectivity under mild conditions.

Catalytic aldol-type reaction of aldehydes with ethyl diazoacetate using quarternary ammonium hydroxide as the base

The direct aldol-type condensation of aldehydes with ethyl diazoacetate (EDA) promoted by an organic base and non-metallic catalyst such as tetrabutylammonium hydroxide (TBAOH) gave β-hydroxy-α-diazocarbonyl compounds with moderate to excellent yields. Furthermore, the reactivity and scope of various phase-transfer catalysts as well as electronically divergent aldehydes are discussed.