3893-35-4

Upstream product

• 103-79-7 1-phenyl-acetone 
• 591-50-4 iodobenzene 
• 170752-47-3 3-diazo-1,1,1-trifluoropentane-2,4-dione 
• 95092-10-7 N-methoxy-N-methyl-2-phenylacetamide 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 624-90-8 Methanesulfonyl azide 

Downstream Products

• 93-58-3 benzoic acid methyl ester 
• 7624-24-0 1-methoxy-1-phenyl-acetone 
• 31508-44-8 2-phenylpropionic acid methyl ester 
• 6493-83-0 2-methoxy-1-phenyl-propan-1-one 
• 768-03-6 Phenyl vinyl ketone 
• 118823-34-0 2-[2-Oxo-1,2-diphenyl-eth-(E)-ylidene]-5,5-diphenyl-[1,3]dithiolan-4-one 
• 118778-94-2 5-Methyl-2-[2-oxo-1,2-diphenyl-eth-(E)-ylidene]-5-phenyl-[1,3]dithiolan-4-one 
• 118778-93-1 2-[2-Oxo-1-phenyl-prop-(E)-ylidene]-5,5-diphenyl-[1,3]dithiolan-4-one 
• 118778-88-4 5-Methyl-2-[2-oxo-1-phenyl-prop-(E)-ylidene]-5-phenyl-[1,3]dithiolan-4-one 
• 118778-89-5 5-Methyl-2-[2-oxo-1-phenyl-prop-(Z)-ylidene]-5-phenyl-[1,3]dithiolan-4-one 
• 27067-36-3 1ref-Acetyl-2trans,3trans-dimethyl-1-phenyl-cyclopropan 
• 113859-95-3 1,2,4-Trimethyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 79823-26-0 1,2,5-Trimethyl-4-phenyl-3-pyrrolcarbonsaeure-ethylester 
• 113859-90-8 3-(2-Oxo-1-phenyl-propylamino)-cyclopent-2-enone 

Relevant academic research and scientific papers

Gold-Catalyzed [3+2]-Annulations of α-Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity

This work reports gold-catalyzed [3+2]-annulations of α-diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]-annulations with α-diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.

Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.

Blue Light-Promoted N?H Insertion of Carbazoles, Pyrazoles and 1,2,3-Triazoles into Aryldiazoacetates

Blue light irradiation of aryldiazoacetates leads to the formation of free carbenes, which can react with carbazoles, pyrazoles and 1,2,3-triazoles to afford the corresponding N?H inserted products. These reactions are performed under air and at room temperature, allowing the mild preparation of a variety of motifs found in biologically relevant targets. (Figure presented.).

Photochemical Doyle-Kirmse Reaction: A Route to Allenes

This Letter describes the metal-free, blue-light-induced [2,3]-sigmatropic rearrangement of sulfonium ylides generated from donor/acceptor diazoalkanes and propargyl sulfides. The reaction furnishes highly functionalized allenes from a broad range of starting materials in decent yield. Mechanistic experiments supported by the literature data suggest singlet carbenes as intermediates in this reaction.

Controllable construction of isoquinolinedione and isocoumarin scaffolds: Via RhIII-catalyzed C-H annulation of N -tosylbenzamides with diazo compounds

A highly efficient protocol for the synthesis of isoquinolinediones by RhIII-catalyzed C-H activation/annulation/decarboxylation of N-tosylbenzamides with diazo compounds is reported. The switchable synthesis of isocoumarins was also achieved successfully via C-H activation/annulation with slight modification of the reaction conditions. Importantly, the synthetic utility of this new reaction was further demonstrated in an atom-economical and operationally convenient total synthesis of a TDP2 inhibitor derivative from commercially available starting materials.

Au Nanoparticle-Catalyzed Insertion of Carbenes from α-Diazocarbonyl Compounds into Hydrosilanes

Supported Au nanoparticles on TiO2 catalyze the insertion of carbenes from α-diazocabonyl compounds into hydrosilanes. It is proposed that the transformation involves two modes of catalytic activation: formation of nucleophilic Au carbenes on the surface of nanoparticle via expulsion of N2 and activation of the Si-H bond of hydrosilane on Au nanoparticle, followed by coupling of the chemisorbed species. No external ligands or additives are required, while the process is purely heterogeneous, thus allowing the recycling and reuse of the catalyst.

Enantioselective Synthesis of 2,2,3-Trisubstituted Indolines via Bimetallic Relay Catalysis of α-Diazoketones with Enones

An efficient asymmetric intramolecular trapping of ammonium ylides of α-diazoketones with enones to synthesize indoline derivatives was realized. A Rh(II)/chiral N,N′-dioxide-Sc(III) complex bimetallic relay catalytic system was established. A series of optically active 2,2,3-trisubstituted indolines were obtained in high yields (up to 99%), good enantioselectivities (up to 99% ee), and excellent diastereoselectivities (up to >19:1 dr) under mild reaction conditions.

Copper-Catalyzed Carbenoid Insertion Reactions of α-Diazoesters and α-Diazoketones into Si-H and S-H Bonds

An efficient copper-catalyzed carbenoid insertion reaction of α-diazo carbonyl compounds into Si-H and S-H bonds was developed. A wide range of α-silylesters and α-thioesters was obtained in high yields (up to 98%) from α-diazoesters using 5 mol% of a simple copper(I) salt as catalyst. Using 0.05 mol% of the same catalyst, α-diazoketones led to α-silylketones in low to good yields (up to 70%).

Enantioselective N-H insertion reaction of α-aryl α-diazoketones: An efficient route to chiral α-aminoketones

A highly enantioselective N-H insertion reaction of α-diazoketones was developed by using cooperative catalysis by dirhodium(II) carboxylates and chiral spiro phosphoric acids. The insertion reaction provides a new access route to diverse chiral α-aminoketones, which are versatile building blocks in organic synthesis, with fast reaction rates, good yields and high enantioselectivity under mild and neutral conditions. Spiro inspiration: A highly enantioselective N-H insertion reaction of α-diazoketones was developed by using cooperative catalysis by dirhodium(II) carboxylates and chiral spiro phosphoric acids. The insertion reaction provides a new access route to diverse chiral α-aminoketones, which are versatile building blocks in the organic synthesis, with fast reaction rates, good yields and high enantioselectivity under mild and neutral conditions.

Synthesis of Aryldiazoacetates through Palladium(0)-Catalyzed Deacylative Cross-Coupling of Aryl Iodides with Acyldiazoacetates

Palladium(0)-catalyzed deacylative cross-coupling of aryl iodides and acyldiazocarbonyl compounds can be achieved at room temperature under mild reaction conditions. The coupling reaction represents a highly efficient and general method for the synthesis of aryldiazocarbonyl compounds, which have found wide and increasing applications as precursors for generating donor/acceptor-substituted metallocarbenes.