20488-11-3

Upstream product

• 1443-80-7 4-cyanophenyl methyl ketone 
• 25309-65-3 4-ethylbenzonitrile 

Downstream Products

• 101219-69-6 4-(1-hydroxyethyl)benzonitrile 
• 1006037-12-2 methyl 4-(1-azidoethyl)benzonitrile 
• 63539-55-9 4-(1-acetoxy-ethyl)-benzonitrile 
• 362052-00-4 2-(4-cyano-phenyl)-propionic acid 
• 3435-51-6 4-ethenylbenzonitrile 

Relevant academic research and scientific papers

Ferric chloride–catalyzed deoxygenative chlorination of carbonyl compounds: A comparison of chlorodimethylsilane and dichloromethylsilane system

Deoxygenative chlorination of carbonyl compounds using the HMe2SiCl/FeCl3/EtOAc and HMeSiCl2/FeCl3/EtOAc systems has been systemically investigated. The HMe2SiCl-FeCl3 system showed the advantages of good substrate applicability, mild reaction conditions, simple operation, low cost, and easy availability of raw materials. Also, it provided a simple and efficient synthesis route for carbonyl deoxychlorination via a one-pot method. Using the HMeSiCl2/FeCl3/EtOAc system, the β-methylchalcone derivative could be obtained in good yields in addition to obtaining the chlorinated compound. Finally, two plausible reaction routes were proposed to describe the formation of the chlorinated compound and the β-methylchalcone derivative.

Ketone-catalyzed photochemical C(sp3)–H chlorination

Photoexcited arylketones catalyze the direct chlorination of C(sp3)–H groups by N- chlorosuccinimide. Acetophenone is the most effective catalyst for functionalization of unactivated C–H groups while benzophenone provides better yields for benzylic C–H functionalization. Activation of both acetophenone and benzophenone can be achieved by irradiation with a household compact fluorescent lamp. This light-dependent reaction provides a better control of the reaction as compared to the traditional chlorination methods that proceed through a free radical chain propagation mechanism.

Silver-Catalyzed C(sp3)-H Chlorination

A silver-catalyzed chlorination of benzylic, tertiary, and secondary C(sp3)-H bonds was developed. The reaction proceeded with as low as 0.2 mol % catalyst loading at room temperature under air atmosphere with synthetically useful functional group compatibility. The regioselectivity and reactivity tendencies suggest that the chlorination proceeded through a radical pathway, but an intermediate alkylsilver species cannot be ruled out.

Reduction of carbonyl to methylene: Organosilane-Ga(OTf)3 as an efficient reductant system

Direct carbonyl reduction to methylene has been achieved by mild reductant system obtained from the combination of organosilane and gallium (III) trifluoromethanesulfonate {Ga(OTf)3}, a water tolerant, recyclable, catalyst. Among a series of organosilanes studied, dimethylchlorosilane (Me 2SiHCl, DMCS) showed the highest efficiency. Both aromatic and aliphatic ketones were effectively reduced to the corresponding methylene products with high functional groups tolerance, under very mild conditions in a relatively short period of time with good to excellent yields. Graphical Abstract: [Figure not available: see fulltext.]

Direct conversion of carbonyl compounds into organic halides: Indium(III) hydroxide-catalyzed deoxygenative halogenation using chlorodimethylsilane

The reaction of carbonyls and chlorodimethylsilane was effectively catalyzed by indium(III) hydroxide and afforded the corresponding deoxygenative chlorination products, in which the carbonyl carbon accepted two nucleophiles (H and Cl) with releasing oxygen. Only In(OH)3 catalyzed the reaction, and typical Lewis acids such as TiCl4, AlCl3, and BF3·OEt2 showed no catalytic activity. The reaction mechanism of this deoxygenative chlorination includes initial hydrosilylation followed by chlorination. Other nucleophiles such as allyl or iodine were available for this methodology. The moderate Lewis acidity of indium catalyst enabled chemoselective reaction, and therefore ester, nitro, cyano, or halogen groups were not affected during the reaction course. Copyright

Novel synthetic usage of indium compounds as catalyst: Reductive deoxygenation of aryl ketones and sec-benzylic alcohols

The combination of chlorodimethylsilane and a catalytic amount of indium compounds is effective for the deoxygenation of aryl ketones and sec-benzylic alcohols to the corresponding hydro- carbons. The combination system is so selective toward carbonyls that the functionalities such as halogen, ester, and ether tolerate the reduction conditions.