94161-45-2

Upstream product

• 34040-64-7 p-methyloxycarbonylbenzyl chloride 
• 98-88-4 benzoyl chloride 
• 70-11-1 α-bromoacetophenone 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 98-86-2 acetophenone 
• 2206-94-2 1-acetoxy-1-phenylethene 
• 619-45-4 4-methoxycarbonyl aniline 
• 42497-80-3 methyl 4-(phenylethynyl)benzoate 
• 536-74-3 phenylacetylene 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 960-16-7 tributylphenylstannane 
• 13939-06-5 molybdenum hexacarbonyl 

Downstream Products

• 1433269-77-2 methyl 4-(2-phenylallyl)benzoate 
• 52380-62-8 1-(4-methoxycarbonylphenyl)-2-phenylethane-1,2-dione 
• 1309977-05-6 C₂₁H₂₃N₃O₃ 

Relevant academic research and scientific papers

Deoxybenzoins from Stille carbonylative cross-couplings using molybdenum hexacarbonyl

Stille-type carbonylative cross-couplings, employing palladium catalysis and Mo(CO)6 as the carbon monoxide carrier, were used for the preparation of deoxybenzoins. Straightforward transformations were conveniently performed in closed vessels at 100 °C, providing the products in good yields. Benzyl bromides and chlorides were used as coupling partners with aryl and heteroaryl stannanes. This mild three-component carbonylation employs the destabilizing agent DBU to promote smooth release of carbon monoxide from Mo(CO)6, which made this protocol operationally simple and minimized the formation of Stille diarylmethane products.

Salicylic Acid-Catalyzed Arylation of Enol Acetates with Anilines

α-Aryl ketones are both structure moieties commonly found in bioactive compounds and versatile synthetic intermediates for the preparation of drug-like molecules. An operationally simple and scalable protocol has been developed to prepare α-aryl ketones from readily available aromatic amines and enol acetates (or silyl enol ethers). This metal-free methodology features the use of salicylic acid as a convenient catalyst to promote the formation of aryl radicals from in-situ generated aryl diazonium salts, without demanding thermal or photochemical activation. The mild reaction conditions used are compatible with anilines substituted with diverse functionalities. Structural elaboration of some prepared α-aryl ketones was accomplished to illustrate their usefulness as building blocks. (Figure presented.).

PtO2/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups

A highly efficient PtO2/PTSA catalyst system for the hydration of a wide array of alkynes was developed. This method proved to be compatible with a large range of functional groups and the ketone products were obtained in high yields. The scope of this methodology was also extended to the synthesis of 3-Aryl-isochromenones,-indoles and-benzofurans.

A Remarkably Simple Hybrid Surfactant-NHC Ligand, Its Gold-Complex, and Application in Micellar Catalysis

A combination of an N-heterocyclic carbene (NHC) ligand and a structurally simple surfactant has been realized, the hybrid surfactant-NHC. The related gold complex was synthesized, fully characterized, and applied in catalysis. This remarkably simple strategy allows, in combination with a co-surfactant, the application of gold catalysis in water. Just merge it! The hybrid of a surfactant and an N-heterocyclic carbene (NHC) ligand is reported and applied for the synthesis of the derived gold complex (see scheme). The new resulting NHC-based metallosurfactant can interact with surfactants to form micelles and allows micellar catalysis for gold catalysis in water.

Alkylations of Arylboronic Acids including Difluoroethylation/Trifluoroethylation via Nickel-Catalyzed Suzuki Cross-Coupling Reaction

An efficient alkylation method of functionalized alkyl halides under mild nickel-catalyzed C(sp3)-(sp2) Suzuki cross-coupling conditions is described. The features of this approach are excellent functional group compatibility, low cost nickel catalyst, and the use of a mild base. This is also the first successful example of the nickel-catalyzed direct 2,2-difluoroethylation or 2,2,2-trifluoroethylation of aryl-/heteroarylboronic acids.

Palladium-catalyzed carbonylative negishi-type coupling of aryl iodides with benzyl chlorides

Do the competition: The synthesis of 1,2-diarylethanones has been accomplished using the palladium-catalyzed coupling of aryl iodides and CO/benzyl chlorides or benzoyl chlorides. These reactions proceed smoothly in the presence of zinc powder to afford the products in moderate to excellent yields.

Direct preparation of benzylic manganese reagents from benzyl halides, sulfonates, and phosphates and their reactions: Applications in organic synthesis

The use of highly active manganese (Mn)*, prepared by the Rieke method, was investigated for the direct preparation of benzylic manganese reagents. The oxidative addition of the highly active manganese to benzylic halides was easily completed under mild conditions. Moreover, benzylic manganese sulfonates and phosphates were prepared by direct oxidative addition of Mn* to the carbon-oxygen bonds of benzylic sulfonates and phosphates. The resulting benzylic manganese reagents were found to undergo cross-coupling reactions with a variety of electrophiles. Most of these reactions were carried out in the absence of any transition metal catalyst under mild conditions. In addition, the use of highly active manganese was also studied for preparation of homo-coupled products of functionalized benzyl halides without transition metal catalysts. These useful approaches provided not only a facile synthetic route to the preparation of resoricinolic lipids but a facile synthesis of functionalized 4-benzylpyridines by regioselective and chemo selective γ-addition of benzylic group to N-alkoxycarbonylpyridinum salts.

Benzylic Manganese Halides, Sulfonates, and Phosphates: Preparation, Coupling Reactions, and Applications in Organic Synthesis

The use of highly active manganese, prepared by the Rieke method, for the direct preparation of benzylic manganese reagents was investigated. The oxidative addition of the highly active manganese (Mn*) to benzylic halides was easily completed under mild conditions. More importantly, benzylic manganese sulfonates and phosphates were prepared by direct oxidative addition of Mn* to the carbon-oxygen bonds of benzylic sulfonates and phosphates. The resulting benzylic manganese reagents were found to undergo cross-coupling reactions with a variety of electrophiles. The majority of these reactions were carried out in the absence of any transition metal catalyst under mild conditions. This approach also provided a facile synthetic route to the preparation of resorcinolic lipids.

Dibenzoyldiazomethane-acridine conjugate: A novel DNA photofootprinting agent

Dibenzoyldiazomethane derivative covalently attached to acridine effectively cleaves DNA by photoirradiation with long wavelength W light (> 400 nm). DNA cleavage experiments using 32P-5'-end-labeled DNA showed that the cleavage by the conjugate is neither sequence nor base selective, indicating that DBDM-acridine conjugate can be used as a photofootprinting agent.

Metallic Nickel-Mediated Synthesis of Ketones by the Reaction of Benzylic, Allylic, Vinylic, and Pentafluorophenyl Halides with Acid Halides

Metallic nickel was investigated as a convenient coupling reagent for the synthesis of ketones by the reaction of benzylic, allylic, vinylic, and pentafluorophenyl halides with acid halides at 85 deg C in glyme.A variety of benzylic ketones with functional groups including halogen, cyano, methoxycarbonyl, and hydroxycarbonyl groups were prepared in good yields by this method.The reaction was demonstrated to proceed via organonickel halide intermediates formed by the smooth oxidative addition of benzylic and acyl halides to metallic nickel, which were trapped with electron-deficient olefins. (?-Allyl)nickel halides, prepared in situ at 85 deg C from allylic halides and the nickel, also worked for the preparation of ketones.Vinylic and pentafluorophenyl halides but not alkyl halides reacted with acid halides to give the corresponding ketones in moderate yields.