23566-47-4

Upstream product

• 35447-68-8 isovaleryl bromide 
• 1004-22-4 (phenylethynyl)sodium 
• 15212-29-0 5-methyl-1-phenyl-1-hexyn-3-ol 
• 536-74-3 phenylacetylene 
• 108-12-3 isopentanoyl chloride 
• 590-86-3 isovaleraldehyde 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 108-64-5 Ethyl isovalerate 
• 816-66-0 4-methyl-2-oxopentanoic acid 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 1597415-48-9 C₁₈H₂₄O₂ 
• 100-52-7 benzaldehyde 
• 7154-75-8 4-methylpentyne 
• 852525-80-5 1-phenyl-5-methyl-2-hexyn-1-ol 

Downstream Products

• 1428337-70-5 C₁₇H₂₂O 
• 1428337-94-3 C₁₇H₂₂O 
• 13893-97-5 1-phenyl-5-methylhexane-1,3-dione 

Relevant academic research and scientific papers

A straightforward synthesis of Ynones by reaction of dimethylalkynylaluminum reagents with acid chlorides

Alkynyldimethylaluminum reagents react with various aromatic and aliphatic acid chlorides in a fast and efficient way. This reaction provides a simple entry to numerous ynones, using readily available, inexpensive, and nontoxic metalating agent, and does not require any transition metal as a catalyst.

Practical synthesis of α,β-Alkynyl ketones by oxidative alkynylation of aldehydes with hypervalent alkynyliodine reagents

A practical, metal-free carbonyl C(sp2)H oxidative alkynylation of aldehydes with hypervalent alkynyliodine reagents without the use of any catalysts is described for the synthesis of various α,β-alkynyl ketones. Here, two different methods have been developed where limiting reagents or substrates can be switched, and adopted according to the valuableness of aldehyde substrates or hypervalent alkynyliodine reagents. These reactions proceed with a broad substrate scope and high functional-group compatibility.

Synthesis of substituted benzo[: B] [1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones

We have developed a novel synthetic method accessing benzo[b][1,4]oxazepines that are one of the rare classes of benzoxazepine derivatives by reaction of 2-aminophenols with alkynones in 1,4-dioxane at 100 °C. A series of benzo[b][1,4]oxazepine derivatives can be prepared by using this synthetic protocol. Mechanistic experiments indicated that the hydroxy proton of the aminophenol could play a crucial role in the formation of an alkynylketimine intermediate that undergoes 7-endo-dig cyclization.

Intramolecular and Ferrier Rearrangement Strategy for the Construction of C1-β-d-xylopyranosides: Synthesis, Mechanism and Biological Activity Study

A stereoselective synthesis of C1-β-d-xylopyranoside derivatives had been developed via intramolecular 1,3-acyloxy migration/Ferrier rearrangement stategy from readily available propargylic carboxylates and d-xylal. A combined catalytic system of chloro(t

Alkynylation of Csp2 (O)–H Bonds Enabled by Photoredox-Mediated Hydrogen-Atom Transfer

The development of new hydrogen-atom transfer (HAT) strategies within the framework of photoredox catalysis is highly appealing for its power to activate a desired C?H bond in the substrate leading to its selective functionalization. Reported here is the first photoredox-mediated hydrogen-atom transfer method for the efficient synthesis of ynones, ynamides, and ynoates with high regio- and chemoselectivity by direct functionalization of Csp2 (O)?H bonds. The broad synthetic application of this method has been demonstrated by the selective functionalization of C(O)?H bonds within complex molecular scaffolds.

Access to Tetronic Acids via Silver-Catalyzed CO2 Incorporation into Conjugated Ynones

Facile and versatile access to highly functionalized tetronic acids has been successfully achieved through the reaction of conjugated ynones with carbon dioxide. In the presence of a base, the enolates generated from the ynones capture CO2 via

Pd-Catalyzed Cross-Coupling of Terminal Alkynes with Chromium(0) Fischer Carbene Complexes

Alkyl chromium(0) carbene complexes typically undergo cycloadditions with alkynes to afford carbo- or heterocyclic compounds. In the presence of Pd catalyst, it is demonstrated that a traditional cycloaddition pathway is completely altered: instead of cyc

Sunlight-Driven Decarboxylative Alkynylation of α-Keto Acids with Bromoacetylenes by Hypervalent Iodine Reagent Catalysis: A Facile Approach to Ynones

A novel and practical decarboxylative alkynylation of α-keto acids with bromoacetylenes is catalyzed by hypervalent iodine(III) reagents when irradiation by sunlight at room temperature. The product ynones are generated in good yields. Experiments show that results obtained with blue light (λ=450-455 nm) are comparable to those obtained when using sunlight. Mechanistic studies demonstrate that the sunlight-driven decarboxylation undergoes a radical process.

Dehydrogenative Meyer-Schuster-like rearrangement: A gold-catalyzed reaction generating an alkyne

Easily accessible propargylic esters are converted to the inverted alkynyl ketones in an oxidative gold-catalyzed reaction. Gagosz's catalyst in combination with PhI(OAc)2 is the best system for this conversion and 18 examples with yields up to 80 % are reported. The results indicate that the triple bond in the product is formed by elimination from a vinylgold intermediate. In a formal sense the new conversion overall is a dehydrogenative Meyer-Schuster rearrangement. It takes alkynes: Propargyl esters can be converted into alkynyl ketones by a new oxidative gold-catalyzed reaction. The best catalyst system is Ph3PAuCl/AgNTf2 in combination with the oxidant PhI(OAc)2. The yields are as high as 80 % and the reaction can be conducted in the presence of air. Copyright

Synthesis of 3-carbonyl pyrazole-5-phosphonates via 1,3-dipolar cycloaddition of Bestmann-Ohira reagent with ynones

The present work explores the hitherto unexplored reactivity of ynones as dipolarophiles with Bestmann-Ohira reagent. The reaction offers a convenient route for the synthesis of regioisomerically pure 3,5-disubstituted or 3,4,5-trisubstituted pyrazoles in