606-86-0

Usage

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 1739, 1994 DOI: 10.1016/0040-4039(94)88333-5

InChI:InChI=1/C21H18O/c22-21(19-14-8-3-9-15-19)16-20(17-10-4-1-5-11-17)18-12-6-2-7-13-18/h1-15,20H,16H2

Upstream product

• 917-64-6 methyl magnesium iodide 
• 106552-33-4 2-bromo-1,3,3-triphenyl-1-propanone 
• 60-29-7 diethyl ether 
• 4747-13-1 α-methoxystyrene 
• 101-81-5 Diphenylmethane 
• 849-01-4 1,3,3-triphenylprop-2-en-1-one 
• 611-91-6 2,3-dibromo-1,3-diphenylpropane-1-one 
• 408521-43-7 2-bromo-1,3,3-triphenyl-propenone 
• 98540-20-6 (Z)-1-methoxy-1,3,3-triphenylpropene 
• 102-92-1 cinnamoyl chloride 
• 71-43-2 benzene 
• 555-54-4 diphenylmagnesium 
• 591-51-5 phenyllithium 
• 614-47-1 1,3-diphenyl-propen-3-one 

Downstream Products

• 64740-35-8 1-oxy-1.1.3.3-tetraphenyl-propane 
• 119-61-9 benzophenone 
• 588-59-0 stilbene 
• 1669-73-4 1,3,3-triphenyl-propan-1-one oxime 
• 106552-33-4 2-bromo-1,3,3-triphenyl-1-propanone 
• 861327-52-8 2-benzhydryl-3-chloro-1,3-diphenyl-propan-1-one 
• 40685-26-5 2-methyl-1,3,3-triphenyl-propan-1-one 
• 55043-63-5 3,3-Diphenylpropiophenon-azin 
• 4960-55-8 1,1,3,3-tetraphenyl-1-propene 
• 5324-00-5 2,3-diphenyl-1H-indene 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 18636-54-9 1,2-diphenyl-1H-indene 
• 849-01-4 1,3,3-triphenylprop-2-en-1-one 
• 6624-02-8 3-hydroxy-1,3,3-triphenyl-propan-1-one 

Relevant academic research and scientific papers

Arylboronic Acid Catalyzed Dehydrative Mono-/Dialkylation Reactions of β-Ketoacids and Alcohols

The dehydrative mono-/dialkylation reactions of alcohols and β-ketoacids were realized under arylboronic acid catalysis, furnishing a series of β-aryl ketones and β-ketoesters in yields of 15–99%, with CO2 and H2O being the byproduct

Visible-Light Photoredox-Catalyzed Dicarbofunctionalization of Styrenes with Oxime Esters and CO2: Multicomponent Reactions toward Cyanocarboxylic Acids and γ-Keto Acids

A photoredox-catalyzed dicarbofunctionalization of styrenes with oxime esters and CO2 has been achieved. Notably, a series of four-, five-, or six-membered cyclic ketone oximes worked well to furnish a wide range of ε-, ζ-, and η-cyanocarboxylic acids in good yields. Furthermore, a series of γ-keto acids also could be obtained by employing acyclic ketone oxime esters as the carbonyl radical precursor. It provides convergent access to diverse biologically important cyanocarboxylic and γ-keto acids.

Merging Pd0/PdII Redox and PdII/PdII Non-redox Catalytic Cycles for the Allylarylation of Electron-Deficient Alkenes

An allylarylation of electron-deficient alkenes with aryl boronates and allylic carbonates has been developed. This method allows access to a wide variety of carbon skeletons from readily available starting materials. Mechanistic studies indicate that this reaction is enabled by a cooperative catalysis based on merging Pd0/PdII redox and PdII/PdII non-redox catalytic cycles.

Beyond the Tebbe Olefination: Direct Transformation of Esters into Ketones or Alkenes

A direct, effective, and operationally simple transformation of esters into ketones or alkenes by the exclusive action of Tebbe's reagent has been developed. The transformation utilizes the dual character of Tebbe's reagent as both a methylenation agent and a rearrangement catalyst in the reaction of a wide range of substituted vinyl ethers. The resulting transformation involves sequential methylenation and rearrangement reactions and it offers a high degree of selectivity toward the synthesis of ketones or alkenes. The scope and limitations of the developed methods have been also examined.

Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME

Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.

Ruthenium-Catalyzed α-Alkylation of Ketones Using Secondary Alcohols to β-Disubstituted Ketones

An assortment of aromatic ketones was successfully functionalized with a variety of unactivated secondary alcohols that serve as alkylating agents, providing β-disubstituted ketone products in good to excellent yields. Remarkably, challenging substrates such as simple acetophenone derivatives are effectively alkylated under this ruthenium catalysis. The substituted cyclohexanol compounds displayed product-induced diastereoselectivity. Mechanistic studies indicate the involvement of the hydrogen-borrowing pathway in these alkylation reactions. Notably, this selective and catalytic C-C bond-forming reaction requires only a minimal load of catalyst and base and produces H2O as the only byproduct, making this protocol attractive and environmentally benign.

Iodine-catalyzed α,β-dehydrogenation of ketones and aldehydes generating conjugated enones and enals

A transition metal-free α,β-dehydrogenation of ketones and aldehydes was developed. This reaction was conducted in a facile I2/KI/DMSO system to produce the corresponding unsaturated compounds in good to high yields. The gram-scale experiment also indicated the potential synthetic value of this new reaction in organic synthesis. In the reaction, DMSO acted as both solvent and mild oxidant.

Palladium-Catalyzed Cascade Reactions of 2-(Cyanomethoxy)chalcones with Arylboronic Acids: Selective Synthesis of Emissive Benzofuro[2,3- c]pyridines

The Pd(II)-catalyzed cascade reactions of 2-(cyanomethoxy)chalcones with arylboronic acids were demonstrated, allowing the rapid construction of benzofuro[2,3-c]pyridine skeletons with excellent selectivity. These transformations involve the domino-style formation of C-C/C-C/C-N bonds through nitrile carbopalladation, intramolecular Michael addition, cyclization, and aromatization. This chemistry allows for the reactions of 2-(cyanomethoxy)chalcones with thiophen-3-ylboronic acid, providing 3-aryl-1-(thiophen-3-yl)benzofuro[2,3-c]pyridines in moderate to good yields. In addition, the resulting products represent a new class of emissive fluorophores.

9-(Diphenylphosphino)anthracene-based phosphapalladacycle catalyzed conjugate addition of arylboronic acids to electron-deficient alkenes

9-(Diphenylphosphino)anthracene-based phosphapalladacycle catalyzed conjugate addition of arylboronic acids to electron-deficient alkenes such asα,β-unsaturated ketones, esters, nitrile and nitroalkenes gave corresponding β-arylated alkanes in good yields and achieved TON up to 700.

Uncatalyzed conjugate addition of organozinc halides to enones in DME: A combined experimental/computational study on the role of the solvent and the reaction mechanism

Both aryl and alkylzinc halides prepared by direct insertion of zinc into organic halides in the presence of LiCl underwent the conjugate addition reaction to nonenolizable unsaturated ketones in excellent yield, provided that DME was used instead of THF as the solvent. Diffusion NMR measurements highlighted that the species undergo considerable aggregation under the experimental conditions used in the synthetic procedure, but no substantial differences have been found between the two solvents. Density functional theory calculations, prompted by the experimental aggregation study, revealed an unexpected reaction mechanism, where the coordinating capabilities of DME stabilize a transition state involving two organozinc moieties, lowering the activation energy of the reaction with respect to that seen for THF, enough to explain the fast and quantitative reactions observed experimentally and the different behaviors of the two solvents.