52267-50-2

Upstream product

• 5396-89-4 benzyl acetoacetate 
• 100-51-6 benzyl alcohol 
• 13407-52-8 2-naphthalenesulphonyl azide 
• 2684-62-0 diazoacetone 
• 124-38-9 carbon dioxide 
• 100-39-0 benzyl bromide 
• 941-55-9 4-toluenesulfonyl azide 

Downstream Products

• 52267-51-3 benzyl diazoacetate 

Relevant academic research and scientific papers

Catalytic Ring Expansion of Activated Heteroarenes Enabled by Regioselective Dearomatization

Catalytic ring expansion of activated heteroarenes through 1,4-dearomative addition of diazoacetates was established for the construction of various fused azepines by an elaborate control of the reaction kinetics at each step. The use of a silver catalyst was essential to drive the overall reaction for generating the desired seven-membered azepines. Because of the excellent substrate scope and selectivity, the developed methodology presents an innovative approach for the synthesis of multifused azepines, which are biologically relevant molecules.

Rh(III)-Catalyzed [5 + 1] Annulation of Indole-enaminones with Diazo Compounds to Form Highly Functionalized Carbazoles

A novel Rh(III)-catalyzed C-H activation/annulation cascade of indole-enaminones with diazo compounds was reported to construct diversely functionalized carbazole frameworks. The most notable characteristic is that this transformation could smoothly furnish a novel [5 + 1] cyclization product with good to excellent yields (up to 95%), accompanied by the thorough removal of acetyl and N,N-dimethyl groups of two substrates from the target products, rather than the normally expected [4 + 2] cyclization products.

Stereoselective bioreduction of α-diazo-β-keto esters

Diazo compounds are versatile reagents in chemical synthesis and biology due to the tunable reactivity of the diazo functionality and its compatibility with living systems. Much effort has been made in recent years to explore their accessibility and synth

Ruthenium(II)-Catalyzed Ortho-C-H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water

Ruthenium(II)-catalyzed ortho-C-H alkylation of naphthylamines with diazo compounds for the synthesis of 2,2-disubstituted π-extended 3-oxindoles has been developed. The method represents the first example of C-H alkylation via carbenoid insertion in wate

Synthesis and use of a cost-effective, aqueous soluble diazo transfer reagent – m-carboxybenzenesulfonyl azide

Herein, we report the preparation and use of m-carboxybenzenesulfonyl azide as a diazo transfer reagent. This compound is an inexpensive and potentially scalable alternative to many of the diazo transfer reagents currently available, most of which have hazards associated with their use. Its usefulness and suitability as a diazo transfer reagent was assessed on the basis of cost, safety and its effectiveness in diazo transfer to a variety of different substrates.

A 'sulfonyl-azide-free' (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis

Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. The first 'sulfonyl-azide-free' (SAFE) protocol for producing diazo compounds from their active-methylene precursors via the Regitz diazo transfer reaction was developed and has displayed a remarkable substrate scope. It can be applied to generating arrays of diazo compounds for further evolution via combinatorial chemistry and a range of scaffold-generating transformations.

Atroposelective Phosphoric Acid Catalyzed Three-Component Cascade Reaction: Enantioselective Synthesis of Axially Chiral N-Arylindoles

An efficient organocatalytic atroposelective three-component cascade reaction of 2,3-diketoesters, aromatic amines, and 1,3-cyclohexanediones has been developed for the highly enantioselective synthesis of axially chiral N-arylindoles. The success of this method derives from the use of a newly developed second-generation chiral spirocyclic phosphoric acid as the catalyst. In addition, this protocol was extended to the synthesis of an axially chiral monophosphorus ligand.

Rh(III)-catalyzed annulation of BOC-protected benzamides with diazo compounds: Approach to isocoumarins

A mild rhodium-catalyzed annulation of Boc-protected benzamides with diazo compounds via C?C/C?O bond formation has been explored. In the presence of [Cp*RhCl2]2, AgSbF6 and Cs2CO3, Boc-protected benzamides can be effectively annulated to yield isocoumarins in 0.5–2 h.

Catalytic Enantioselective Cloke–Wilson Rearrangement

Racemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of a chiral phosphoric acid as the catalyst. The reaction involves activation of the donor-acceptor cyclopropane substrate by the

Synthesis of 1 H-Pyrrol-3(2 H)-ones via Three-Component Reactions of 2,3-Diketo Esters, Amines, and Ketones

An efficient one-pot, three-component reaction of 2,3-diketo esters with amines and ketones has been developed for the synthesis of 1H-pyrrol-3(2H)-ones. By using trifluoroacetic acid (TFA) as the additive and acetonitrile (MeCN) as the solvent, this conv