101640-65-7

Upstream product

• 4773-82-4 2,3-dimethyl-1H-indene 
• 29539-21-7 3-methylisocoumarin 
• 917-54-4 methyllithium 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 123-54-6 acetylacetone 
• 88-67-5 2-Iodobenzoic acid 
• 75-16-1 methylmagnesium bromide 
• 42498-48-6 (Z)-4-difluoroboranyloxy-pent-3-en-2-one 
• 71-43-2 benzene 
• 159050-30-3 2a,7a-Dimethyl-7,7a-dihydro-2aH-1,2-dioxa-cyclobuta[a]indene 
• 19164-66-0 1-Acetoxy-1-methyl-1,2-dihydro-benzocyclobuten 
• 171258-00-7 2-(prop-1-yn-1-yl)-1-acetylbenzene 

Downstream Products

• 14250-05-6 1,8-Dimethyl-chrysen 
• 1262236-73-6 6-aceto-12H-11-methylbenzo[g]pyrido[2,1-b]quinazoline-12-one 
• 1721-94-4 1,3-dimethylisoquinoline 

Relevant academic research and scientific papers

Donor-Flexible Bis(pyridylidene amide) Ligands for Highly Efficient Ruthenium-Catalyzed Olefin Oxidation

An exceptionally efficient ruthenium-based catalyst for olefin oxidation has been designed by exploiting N,N′-bis(pyridylidene)oxalamide (bisPYA) as a donor-flexible ligand. The dynamic donor ability of the bisPYA ligand, imparted by variable zwitterionic and neutral resonance structure contributions, paired with the redox activity of ruthenium provided catalytic activity for Lemieux–Johnson-type oxidative cleavage of olefins to efficiently prepare ketones and aldehydes. The ruthenium bisPYA complex significantly outperforms state-of-the-art systems and displays extraordinary catalytic activity in this oxidation, reaching turnover frequencies of 650 000 h?1 and turnover numbers of several millions.

Enantioselective Synthesis of 1,2-Dihydronaphthalenes via Oxidative N-Heterocyclic Carbene Catalysis

1,2-Dihydronaphthalenes are important molecules in both medicinal and synthetic chemistry, but methods for the catalytic asymmetric construction of this class of molecules are limited. The diastereo- and enantioselective N-heterocyclic carbene-catalyzed cascade annulation reactions using benzodiketones and enals under oxidative conditions, which afford a variety of 1,2-dihydronaphthalenes with two adjacent stereocenters in up to 99% yield, with >20:1 dr, and up to 99% ee, are reported. Furthermore, the product can be easily transformed to a series of useful compounds such as alcohol, amide, and epoxide.

Tandem carbon-carbon bond insertion and intramolecular aldol reaction of benzyne with aroylacetones: Novel formation of 4,4′-disubstituted 1,1′-binaphthols

An efficient route to 4-aryl-2-naphthols from arynes and aroylacetones was developed by carbon-carbon bond insertion followed by an intramolecular aldol reaction and dehydration. Benzyne derived from 2-(trimethylsilyl)phenyl triflate reacted with benzoyla

Effective cleavage of ditertiary glycols via vanadium(V)-catalyzed aerobic oxidation

The aerobic oxidation of ditertiary glycols catalyzed by oxytrichlorovanadium resulted in carbon-carbon bonds cleavage producing the ketones efficiently.

Three component reaction of arynes with cyclic ethers and active methines: Synthesis of ω-trichloroalkyl phenyl ethers

Synthesis of ω-chlorinated alkyl phenyl ethers by tandem reaction of arynes with cyclic ethers and active methines was achieved. Reaction of benzenediazonium 2-carboxylate with tetrahydropyran or tetrahydrofuran in refluxing chloroform afforded 6,6,6-trichlorohexyl phenyl ether or 5,5,5-trichloropentyl phenyl ether in 40% and 61% yields, respectively. When dichloroacetonitrile was used as a reactant, 5,5-dichloro-5-cyanopentyl phenyl ether was obtained in 61% yield. While benzenediazonium carboxylate did not react with epoxides, reaction of benzyne derived from 2-(trimethylsilyl)phenyl triflate with epoxides afforded 3,3,3-trichloropropyl phenyl ethers in good yields as isomeric mixtures. The reaction of oxetanes with benzyne was also reported.

Platinum-catalyzed chemoselectively hydrative dimerization of 2-alkynyl-1-acetylbenzenes for one-pot facile synthesis of chrysene derivatives

(Chemical Equation Presented) We report one-pot syntheses of chrysene compounds via PtCl2-catalyzed hydrative dimerization of readily available 2-alkynyl-1-acetylbenzenes. This new tandem catalysis comprises an initial selective hydration of th

Facile insertion reaction of arynes into carbon-carbon σ-bonds

The carbon-carbon σ-bond of various β-dicarbonyl compounds was found to add to the triple bond of arynes under extremely mild conditions, leading to direct introduction of different carbon functional groups into the aromatic skeletons. The Royal Society o

The photoaddition of 1,3-diketonatoboron difluorides with benzene derivatives

The boron difluoride complexes of 2-acetylcyclohexanone, 2-acetylcyclopentanone, and acetylacetone (abbreviated as ACHBF2, ACPBF2, and AABF2) were irradiated in the presence of benzene to give 1:1 adducts as the primary photoadducts; for certain BF2 complexes, toluene, chlorobenzene, benzonitrile, and methyl benzoate were also used as substrates.The 1,5-diketone photoadducts were assumed to form by a photocycloaddition followed by cyclobutane opening and hydrolysis to give 1,2 adducts.They undergo a variety of secondary thermal reactions, probably acid catalyzed, to give enol ethers, enol acetates, acetophenones, and ketonylacetophenones.The efficiency of these secondary reactions determines the final products.Photoaddition with a monosubstituted benzene preferentially occurs at the 3,4 bond without regioselectivity.Under oxygen, ACHBF2 photolytically reacts with benzene to give a secondary oxidation product of a 10-membered cyclic alkylphenone, which is proven by X-ray crystallographic analysis to have the benzene ring and carbonyl group in orthogonal orientation.It is shown that the singlet excited state ACHBF2 initiates the photoaddition, probably through the formation of the benzene exciplex, which could be detected by its emission.While the Stern-Volmer rates are small, the quantum yield of photoaddition products is as high as 0.12-0.19 under limiting conditions.

PHOTOOXIDATION OF SUBSTITUTED INDENES AT LOW TEMPERATURE

1,2-, 1,4- and ene products were obtained on photooxidation of 2,3-dimethylindene and 3-tert-butylindene at low temperature.The product distribution depends on solvent.