109600-55-7

Upstream product

• 644-34-8 3,4-methylenedioxychalcone 
• 7664-93-9 sulfuric acid 
• 644-34-8 (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-phenylprop-2-en-1-one 
• 141-78-6 ethyl acetate 
• 7315-32-4 5-vinyl-1,3-benzodioxole 
• 93-97-0 benzoic acid anhydride 
• 495-76-1 piperonol 
• 98-85-1 1-Phenylethanol 
• 120-57-0 piperonal 
• 98-86-2 acetophenone 
• 67-56-1 methanol 
• 109-77-3 malononitrile 
• 30830-55-8 3-(3,4-methylenedioxyphenyl)propionaldehyde 
• 7031-03-0 3-(benzo[d][1,3]dioxol-5-yl)propan-1-ol 

Downstream Products

• 644-34-8 (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-phenylprop-2-en-1-one 
• 864758-71-4 5-benzo[1,3]dioxol-5-yl-3-phenylpent-1-yn-3-ol 

Relevant academic research and scientific papers

Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water

Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.

Nickel-catalyzed α-alkylation of ketones with benzyl alcohols

We reported an efficient method for α-alkylation of ketones with benzyl alcohols using the pyridine-bridged pincer-type N-heterocyclic carbenes nickel complexes as catalysts. A wide range of ketones and benzyl alcohols were efficiently converted into various alkylated products in moderate to high yields. In addition, these nickel complexes were also successfully applied for the synthesis of a wide range of quinoline derivatives.

Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol

The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.

Method for preparing alpha-alkyl substituted ketone compound

The invention relates to a method for preparing an alpha-alkyl substituted ketone compound, which comprises the following steps: preparing a primary alcohol compound and a secondary alcohol compound as raw materials, adding alkali; with a cyclic iridium complex as a catalyst and water as a reaction medium, heating and stirring the mixture and reacting for 10 to 24 hours under the protection of inert gas, and cooling a reaction product to room temperature after the reaction is finished; carrying out reduced pressure distillation and concentration to obtain a crude product, and carrying out column chromatography purification to obtain a series of alpha alkyl substituted ketone compounds. The method is simple to operate, available in raw materials, low in price, high in reaction efficiency and selectivity, good in adaptability to various functional groups and wide in substrate universality; since water is used as a reaction medium to meet the green and environment-friendly requirements, the method is environmentally friendly and is carried out at gram level, so that the potential of industrially synthesizing the alpha alkyl substituted ketone compound is achieved; therefore, The method has expanded application in the fields of medicines, organic synthesis and the like.

Sustainable and Selective Alkylation of Deactivated Secondary Alcohols to Ketones by Non-bifunctional Pincer N-heterocyclic Carbene Manganese

A sustainable and green route to access diverse functionalized ketones via dehydrogenative–dehydrative cross-coupling of primary and secondary alcohols is demonstrated. This borrowing hydrogen approach employing a pincer N-heterocyclic carbene Mn complex displays high activity and selectivity. A variety of primary and secondary alcohols are well tolerant and result in satisfactory isolated yields. Mechanistic studies suggest that this reaction proceeds via a direct outer-sphere mechanism and the dehydrogenation of the secondary alcohol substrates plays a vital role in the rate-limiting step.

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.

Celite-Polyaniline supported palladium catalyst for chemoselective hydrogenation reactions

Polyaniline coated on particles of celite is used as support to load palladium catalyst. This heterogenized Celite?PANI?Pd system, is used as an efficient catalyst for chemoselective hydrogenation reactions. The catalyst is characterized by usual spectral, analytical techniques and studied for hydrogenation reactions at ambient conditions. The mild reaction conditions allow the control over the reactions and excellent selectivity is achieved in number of conversions. Hydrogenation of a carbon–carbon double bond was favored over other polar π-bond systems, while labile functional groups such as benzyl ether, benzyl esters, cyano, nitro and halogen remained unaffected. Primary amines were converted to N,N-dimethyl amines with formaldehyde, the double bond of coumarin was selectively hydrogenated without opening of the lactone functionality.

Diels-Alder route to norbornane derived vicinal phosphane/borane frustrated Lewis pairs for the metal-free catalytic hydrogenation of α, β-unsaturated ketones

The [4+2] cycloaddition reaction of the (dimesitylphosphino)cyclopentadienes 5a,b with N-phenylmaleimide gave the norbornene derivative 9. Its reduction with LiAlH4 produced the N-phenylpyrrolidino-annulated system 10. Treatment with Piers' bor

Selective Ketone Formations via Cobalt-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols

A homogeneous cobalt-catalyzed β-alkylation of secondary alcohols with primary alcohols to selectively synthesize ketones via acceptorless dehydrogenative coupling is reported for the first time. Notably, this transformation is environmentally benign and atom economical with water and hydrogen gas as the only 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.