113709-54-9

Upstream product

• 67-56-1 methanol 
• 38661-84-6 (E)-1,4-diphenylbut-1-en-3-one 
• 13343-79-8 (E)-1,4-Diphenylbut-1-en-3-yne 
• 1074-12-0 phenylglyoxal hydrate 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 100-52-7 benzaldehyde 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 13343-78-7 1,4-diphenylbut-3-en-1-yne 
• 96-09-3 styrene oxide 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 51034-71-0 <1-2H>phenylglyoxal 

Downstream Products

• 53399-10-3 (E)-2-phenyl-3-styrylquinoxaline 
• 1165-53-3 1,2,4-triphenylbenzene 
• 614-47-1 1,3-diphenyl-propen-3-one 

Relevant academic research and scientific papers

Synthesis of 1,2-Diketones via a Metal-Free, Visible-Light-Induced Aerobic Photooxidation of Alkynes

1,2-Diketones were synthesized by the oxidation of corresponding alkynes using air as the oxidant under metal-free conditions upon irradiation of blue light. A cheap and readily available organic dye, eosin Y, was used as the photocatalyst. For various substituents on the aryl ring, the reaction proceeded smoothly to give the dicarbonylation products in moderate to good yields. Some oxidation-sensitive groups, such as formyl and the carbon-carbon double bond, were tolerated under the developed reaction conditions.

Synthesis of 1,2-Dicarbonyl-3-enes by Hydroacylation of 1-Alkynes with Glyoxal Derivatives Using Metal-Organic Framework Cu/MOF-74 as Heterogeneous Catalyst

A crystalline copper-based metal-organic framework Cu/MOF-74 was synthesized, and used as an efficient heterogeneous catalyst for the synthesis of 1,2-dicarbonyl-3-enes by means of the hydroacylation of 1-alkynes with glyoxal derivatives in the presence o

Chemoselective oxidation of carbon-carbon double or triple bonds to 1,2-diketones with DMSO-based reagents

HBr/DMSO selectively oxidizes the double bond in (E)-1-(2-phenylethenyl)-4-(phenylethynyl)benzene (1) to 1,2-diketone 2. However, 12/DMSO and PdCl2/DMSO oxidize only the triple bond in 1 to 1,2-diketone 3. A similar trend of chemoselectivity is shown for the oxidation of (E)-1,4-diphenyl-1-buten-3-yne (6) with the DMSO-based reagents.

Synthesis of Ketones by C?H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions

A method for the synthesis of ketones from aldehydes and boronic acids via a transition-metal-free C?H functionalization reaction is reported. The method employs nitrosobenzene as a reagent to drive the simultaneous activation of the boronic acid as a boronate and the activation of the C?H bond of the aldehyde as an iminium species that triggers the key C?C bond-forming step via an intramolecular migration from boron to carbon. These findings constitute a practical, scalable, and operationally straightforward method for the synthesis of ketones.

Metal-Free Iodine-Catalyzed Oxidation of Ynamides and Diaryl Acetylenes into 1,2-Diketo Compounds

Metal-free oxidation of ynamides is described, employing pyridine-N-oxides as oxidants under molecular iodine catalysis. In stark contrast to Br?nsted acid catalysis, iodophilic activation of ynamides diverts the reaction manifold into a dioxygenation pathway. This oxidation is very rapid at room temperature with only 2.5 mol % I2. Furthermore, this protocol could be extended to nonactivated alkynes, such as diarylacetylenes, to deliver various benzil derivatives.

N-Heterocyclic Carbene-Catalyzed Umpolung of β,?-Unsaturated 1,2-Diketones

The umpolung of β,?-unsaturated diketones through N-heterocyclic carbene catalysis is described, which allows access to a variety of highly functionalized bicyclic cyclohexene-β-lactones and 1,3,4-triaryl benzenes. An unprecedented reaction pattern involv

A Desulfonylative Approach in Oxidative Gold Catalysis: Regiospecific Access to Donor-Substituted Acyl Gold Carbenes

Donor-substituted acyl gold carbenes are challenging to access selectively by gold-promoted intermolecular oxidation of internal alkynes as the opposite regioisomers frequently predominate. By using alkynyl sulfones or sulfonates as substrates, the oxidative gold catalysis in the presence of substituted pyridine N-oxides offers regiospecific access to acyl/aryl, acyl/alkenyl, and acyl/alkoxy gold carbenes by in situ expulsion of sulfur dioxide. The intermediacies of these reactive species are established by their reactivities, including undergoing further oxidation by the same oxidant, cyclopropanation of styrenes, engaging in a [3+2] cycloaddition with α-methylstyrene, and conversion into dienones. Accept it: A desulfonylative approach was developed to regiospecifically access these underexplored acyl gold carbenes from either alkynyl aryl/alkenyl sulfones or alkynyl sulfonate substrates. The reactivities of these donor- and acceptor-substituted carbenes are examined.

Gold(I)-catalyzed diastereoselective hydroacylation of terminal alkynes with glyoxals

The reaction of an α-ketoaldehyde and a terminal alkyne in the presence of piperidine and a catalytic amount of AuCl delivers 1,2-dicarbonyl-3-enes, products of the formal hydroacylation of the triple bond. The scope of the method is broad; different aryl substituents on the dicarbonyl unit and on the alkyne are well tolerated. The products can be transformed selectively into vinylquinoxalines. Mechanistic studies, including isotope-labeling experiments, indicate that after an initial A3-type conversion to propargylic amines, a subsequent base-mediated alkyne-to-allene isomerization and a hydrolysis of the enamine substructure during the workup deliver the formal hydroacylation products. The simple AuCl catalyst and piperidine convert terminal alkynes and α-ketoaldehydes into 1,2-dicarbonyl-3-enes, the products of a formal hydroacylation of the triple bond, with excellent regio- and diastereoselectivity. There is no evidence for classical A3 coupling products, which could be expected from such a gold-catalyzed reaction of an aldehyde, an amine, and a terminal alkyne. Copyright

CuBr-promoted formal hydroacylation of 1-alkynes with glyoxal derivatives: An unexpected synthesis of 1,2-dicarbonyl-3-enes

An efficient and concise protocol has been developed for the highly regio- and stereoselective synthesis of E-1,2-dicarbonyl-3-ene derivatives by a copper-promoted reaction of 1-alkynes with α-carbonyl aldehydes in the presence of morpholine. The products obtained are believed as the formal hydroacylation of the triple bond.

Ruthenium-catalyzed oxidation of a carbon-carbon triple bond: Facile syntheses of alkenyl 1,2-diketones from alkynes

A new oxidation procedure of alkynes catalyzed by Tp(PPh 3)(CH3CN)Ru-Cl is presented, which provides an efficient way to obtain alkenyl 1,2-diketones via ruthenium alkenyl 1,2-diketone intermediates. In contrast, the analogous reacti