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Upstream product

• 7446-70-0 aluminium trichloride 
• 104095-33-2 3-benzoyl-5-chloromethyl-dihydro-furan-2-one 
• 71-43-2 benzene 
• 123994-49-0 3,4-dihydro-1-naphthyl triflate 
• 100-51-6 benzyl alcohol 
• 50361-53-0 1-(trimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile 
• 50341-99-6 1,2,3,4-tetrahydronaphthalene-1-carbonyl chloride 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 

Relevant academic research and scientific papers

Water as a proton mediator for dioxygen-selective oxidation of alcohols by a planar dinuclear butterfly-like CuCu bonding complex: A combined experimental and computational study

The selective catalytic oxidation of alcohols is important both in laboratory and industrial production, and traditional oxidants cause environmentally lethal wastes. The development of dioxygen selective oxidation efficient has been pursued from atom-efficient, economic and environmental view of points. Using DFT calculation and ESI-MS experiments, we studied the activation of the CuCu bonded planar complex Cu2(ophen)2 to dioxygen and the application of the dioxygen-copper system for the selective oxidation of alcohols. For practical application and green chemistry, this catalytic system avoided the use of a large excess of base and expensive nitroxyl derivatives. In the cycle of oxidation, two oxidative dehydrogenation processes featuring superoxide/peroxide (I) and hydroperoxide (II) occurred along with a series of conformational changes of the butterfly-like Cu-complex from stretched to folded to stretched. Additionally, we characterized the role of the water molecule as a proton mediator in the dioxygen-copper system.

Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols

An intermolecular coupling of primary alcohols and organotriflates has been developed to provide ketones by the action of a Ni(0) catalyst. This oxidative transformation is proposed to occur by the union of three distinct catalytic cycles. Two competitive oxidation processes generate aldehyde in situ via hydrogen transfer oxidation or (pseudo)dehalogenation pathways. As aldehyde forms, a Ni-catalyzed carbonyl-Heck process enables formation of the key carbon-carbon bond. The utility of this rare alcohol to ketone transformation is demonstrated through the synthesis of diverse complex and bioactive molecules.

Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols

An intermolecular coupling of primary alcohols and organotriflates has been developed to provide ketones by the action of a Ni(0) catalyst. This oxidative transformation is proposed to occur by the union of three distinct catalytic cycles. Two competitive oxidation processes generate aldehyde in situ via hydrogen transfer oxidation or (pseudo)dehalogenation pathways. As aldehyde forms, a Ni-catalyzed carbonyl-Heck process enables formation of the key carbon-carbon bond. The utility of this rare alcohol to ketone transformation is demonstrated through the synthesis of diverse complex and bioactive molecules.

Et2Zn-mediated rearrangement of bromohydrins

(Chemical Equation Presented) A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH 2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.

Conversion of ketone trimethylsilylcyanohydrins to several types of compounds

Cyclic ketone O-trimethylsilylcyanohydrins (2) were prepared and converted to various compounds: α-hydroxyketones (3), dehydroxylated ketones (4), α,β-unsaturated ketones (9), tricyclic ketones (10), 1-ethoxycarbonyl-4- phenyl-1,2,4a,5,6,7,8,8a-octahydro-2-naphthalenone (13), 1- phenylperhydroisocoumarin (18) and 1,2,3,4,4a,10,11,11a-octahydro-5h- benzo[a,d]cyclohepten-10-one (20).