79566-35-1

Upstream product

• 49629-37-0 (E)-2-(4-methoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 105-13-5 4-Methoxybenzyl alcohol 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 49629-37-0 2-(4-methoxybenzylidene)-1-tetralone 

Downstream Products

• 1040749-10-7 2-(4-methoxybenzyl)-1-trimethylsilyoxytetral-1-ene 
• 1111116-16-5 2-(4-(methoxyphenyl)methyl)-2-(phenylethynyl)-3,4-dihydronaphthalen-1(2H)-one 

Relevant academic research and scientific papers

Nickel-Catalyzed Selective Synthesis of α-Alkylated Ketones via Dehydrogenative Cross-Coupling of Primary and Secondary Alcohols

Herein, we describe an isolable, air-stable, homogeneous, nickel catalyst that performs dehydrogenative cross-coupling reaction between secondary and primary alcohols to result α-alkylated ketone products selectively. The sequence of steps involve in this one-pot reaction is dehydrogenation of both alcohols, condensation between the ketone and the aldehyde, and hydrogenation of the in situ-generated α,β-unsaturated ketone. Preliminary mechanistic investigation hints a radical mechanism following borrowing hydrogen reaction. (Figure presented.).

Asymmetric Hydrogenation of Racemic Allylic Alcohols via an Isomerization-Dynamic Kinetic Resolution Cascade

Prochiral racemic allylic alcohols are converted to enantioenriched chiral alcohols bearing adjacent stereocenters catalyzed by a diamine diphosphine Ru complex in the presence of tBuOK. The protocol features a broad substrate scope (56 examples) and high

Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori-Ikariya Ru(II) Complexes: One-Pot Reduction of C═C and C═O bonds

3-Arylidenechroman-4-ones and 2-arylidene-1-tetralones are hydrogenated to cis-benzylic alcohols in dr's and er's up to 99:1 via a C═C and C═O one-pot reduction in the presence of 2-5 mol % Noyori-Ikariya-type RuII chiral complexes and HCO2Na as a hydroge

A simple iron-catalyst for alkenylation of ketones using primary alcohols

Herein, we developed a simple iron-catalyzed system for the α-alkenylation of ketones using primary alcohols. Such acceptor-less dehydrogenative coupling (ADC) of alcohols resulted in the synthesis of a series of important α,β-unsaturated functionalized ketones, having aryl, heteroaryl, alkyl, nitro, nitrile and trifluoro-methyl, as well as halogen moieties, with excellent yields and selectivity. Initial mechanistic studies, including deuterium labeling experiments, determination of rate and order of the reaction, and quantitative determination of H2 gas, were performed. The overall transformations produce water and dihydrogen as byproducts.

Synthesis and Structures of Arene Ruthenium (II)–NHC Complexes: Efficient Catalytic α-alkylation of ketones via Hydrogen Auto Transfer Reaction

A panel of six new arene Ru (II)-NHC complexes 2a-f, (NHC?=?1,3-diethyl-(5,6-dimethyl)benzimidazolin-2-ylidene 1a, 1,3-dicyclohexylmethyl-(5,6-dimethyl)benzimidazolin-2-ylidene 1b and 1,3-dibenzyl-(5,6-dimethyl)benzimidazolin-2-ylidene 1c) were synthesized from the transmetallation reaction of Ag-NHC with [(η6-arene)RuCl2]2 and characterized. The ruthenium (II)-NHC complexes 2a-f were developed as effective catalysts for α-alkylation of ketones and synthesis of bioactive quinoline using primary/amino alcohols as coupling partners respectively. The reactions were performed with 0.5?mol% catalyst load in 8?h under aerobic condition and the maximum yield was up to 96%. Besides, the different alkyl wingtips on NHC and arene moieties were studied to differentiate the catalytic robustness of the complexes in the transformations.

NNN pincer Ru(II)-complex-catalyzed α-alkylation of ketones with alcohols

A series of novel ruthenium(II) complexes supported by a symmetrical NNN ligand were prepared and fully characterized. These complexes exhibited good performance in transfer hydrogenation to form new C-C bonds using alcohols as the alkylating agents, generating water as the only byproduct. A broad range of substrates, including (hetero)aryl- or alkyl-ketones and alcohols, were well tolerated under the optimized conditions. Notably, α-substituted methylene ketones were also investigated, which afforded α-branched steric hindrance products. A potential application of α-alkylation of methylene acetone to synthesize donepezil was demonstrated, which provided the desired product in 83% yield. Finally, this catalytic system could be applied to a one-pot double alkylation procedure with sequential addition of two different alcohols. The current protocol is featured with several characteristics, including a broad substrate scope, low catalyst (0.50 mol %) loadings, and environmental benignity.

Method for preparing substituted ketone compound through oxidization, dehydration and alkylation of secondary alcohol

The invention discloses a method for preparing a substituted ketone compound through oxidization, dehydration and alkylation of secondary alcohol, and by means of the green synthetic method, substituted ketones are prepared from primary alcohol and the secondary alcohol through a dehydration C-alkylation-oxidization cascade reaction with the existence of alkali but without a transitional metal catalyst. According to the method, the alcohols which are low in price, easy to obtain, wide in source, stable and low in toxicity are used as alkylation reagent, common base metal inorganic base is used as an additive, methylbenzene is used as solvent, air is economical and safe oxidant, and the corresponding substituted ketone compound with secondary alcohol beta alkylated is directly synthesized through the dehydration C-alkylation-oxidization cascade reaction. The reaction method and condition are simple, no transitional metal catalyst is need, no inert gas protection is needed, the method is easy to operate, the by-product is water, compared with a precious metal catalyst, the inorganic base which is used is low in price and easy to obtain and can be removed conveniently through washing, and no heavy metal residue exists in the final product. Therefore, the method is wide in application scope and has certain research and industrial application prospect.

Catalyst-free dehydrative α-alkylation of ketones with alcohols: Green and selective autocatalyzed synthesis of alcohols and ketones

Direct dehydrative α-alkylation reactions of ketones with alcohols are now realized under simple, practical, and green conditions without using external catalysts. These catalyst-free autocatalyzed alkylation methods can efficiently afford useful alkylated ketone or alcohol products in a one-pot manner and on a large scale by Ci￡C bond formation of the in situ generated intermediates with subsequent controllable and selective Meerwein-Pondorf-Verley-Oppenauer-type redox processes. Plain and simple: The title reaction has been realized under simple and practical conditions without using external catalysts, and can afford alkylated ketone or alcohol products in a one-pot manner and on a large scale. The reaction proceeds by Ci￡C bond formation of the in situ generated intermediates with subsequent controllable and selective Meerwein-Pondorf-Verley-Oppenauer-type redox processes. Copyright

Gold-catalyzed consecutive [1,2] alkyl migration-oxygen transfer reaction of 2-alkynyl-1-tetralones

Gold-catalyzed isomerization of 2-alkynyl-1-tetralones afforded the corresponding 2-naphthylmethyl ketones in good to high yields. For example, the reaction of 2-{4-(methoxyphenyl)methyl}-2-(phenylethynyl)-3,4-dihydronaphthalen-1(2H)-one and 2-benzyl-2-(p

Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles

(Chemical Equation Presented) Catalytic variant: Allyl silanes and silyl enol ethers 1 are good substrates for the catalytic highly enantioselective fluorodesilylation using a combination of a biscinchona alkaloid, N-fluorobenzenesulfonimide (NFSI), and base (see scheme). Pharmaceutically attractive 3-aryl-3-fluorooxindoles such as 3 can also be synthesized with high enantioselectivity.