52958-87-9

Upstream product

• 64432-52-6 2-Benzyl-3-phenyl-2-phenylselanyl-propionitrile 
• 138597-12-3 3-acetoxy-2-methylene-3-phenylpropionitrile 
• 23974-72-3 sodium phenylselenide 
• 53097-56-6 2-benzyl-3-phenylpropionitrile 
• 42550-72-1 methyl 2-benzyl-2-cyano-3-phenylpropionate 
• 102-04-5 1,3-Diphenylpropanone 
• 849943-87-9 (Z)-1,3-diphenylprop-1-en-2-yl 4-methylbenzenesulfonate 
• 557-21-1 zinc(II) cyanide 
• 645-59-0 dihydrocinnamonitrile 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 33695-47-5 (phenylselenenyl)acetonitrile 
• 19362-96-0 2-(1-hydroxybenzyl)acrylonitrile 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

Nickel-Catalyzed Cyanation of Phenol Derivatives with Zn(CN)2 Involving C-O Bond Cleavage

An efficient nickel-catalyzed cyanation of aryl sulfonates, fluorosulfonates, and sulfamates with Zn(CN)2 was developed, which provides a facile access to the nitrile products in generally good to excellent yields. The reaction is accomplished by using NiII complex as the precatalyst and DMAP as the additive. The method also displays wide functional group compatibility; for example, keto, methoxy, N,N-dimethylamino, cyano, ester, and pyridyl groups are well-tolerated during the reaction process.

Preparing method of aromatic nitrile or alkenyl nitrile compound

The invention discloses a preparing method of an aromatic nitrile or alkenyl nitrile compound. The preparing method comprises the following step that under protection of inert gas, an aryl or heteroaryl sulphonate compound shown in a formula II or an alkenyl sulphonate compound shown in a formula IV and a cyanation reagent are subjected to a cross-coupling reaction as is shown below in a solvent under the condition of the presence of a nickel complex, metal zinc and an additive to obtain the aromatic nitrile or alkenyl nitrile compound, wherein 4-dimethylamiopryidine (DMAP) is adopted as the additive, and zinc cyanide is adopted as the cyanation reagent. By means of the preparing method, cyanation of aryl sulphonate, heteroaryl sulphonate or alkenyl sulphonate can be simply and efficientlyachieved with a cheap catalysis system; moreover, the functional group compatibility and substrate universality are good, and a better application prospect and higher using value are provided for achieving industrial synthesis of the aromatic nitrile or alkenyl nitrile compound.

Manganese Catalyzed α-Olefination of Nitriles by Primary Alcohols

Catalytic α-olefination of nitriles using primary alcohols, via dehydrogenative coupling of alcohols with nitriles, is presented. The reaction is catalyzed by a pincer complex of an earth-abundant metal (manganese), in the absence of any additives, base, or hydrogen acceptor, liberating dihydrogen and water as the only byproducts.

Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles

A highly practical and general palladium-catalyzed methodology for the α,β-dehydrogenation of esters and nitriles is reported. Generation of a zinc enolate or (cyanoalkyl)zinc species followed by the addition of an allyl oxidant and a palladium catalyst results in synthetically useful yields of α,β-unsaturated esters, lactones, and nitriles. Preliminary mechanistic investigations are consistent with reversible β-hydride elimination and turnover-limiting, propene-forming reductive elimination.

An α-Diaminoboryl carbanion assisted stereoselective single-pot preparation of α,β-disubstituted Acrylonitriles

An α-diaminoboryl carbanion-mediated one-pot olefination directly converts an acetonitrile or the homologous nitrile into a series of α,β-disubstituted acrylonitriles in a stereo-selective manner. The protocol involves the formation of an α-substituted α-diaminoboryl acetonitrile and subsequent olefination with an aldehyde. The use of an aryl or conjugated aldehyde preferentially leads to a (Z)-acrylonitrile, while an aliphatic aldehyde gave an (E)-isomer as a major product. Two complementary approaches, a linear method and a divergent method, are developed.

Rhodium fluorapatite catalyst for the synthesis of trisubstituted olefins via cross coupling of Baylis-Hillman adducts and arylboronic acids

(Chemical Equation Presented) Treatment of fluorapatite (prepared by incorporating basic species F- in apatite in situ by coprecipitation) with an aqueous solution of RhCl3 resulted in rhodium-exchanged fluorapatite catalyst (RhFAP),

Fe3+-K-10 montmorillonite clay catalyzed Friedel-Crafts reaction of unactivated Baylis-Hillman adducts: An efficient stereoselective synthesis of trisubstituted alkenes containing a benzyl substituent

The stereoselective synthesis of trisubstituted alkenes containing a benzyl substituent has been achieved by employing Friedel-Craft reaction of aromatic compounds with unactivated Baylis-Hillman adducts in the presence of Fe 3+-K-10 montmorill

Friedel-Crafts reaction of the Baylis-Hillman adducts of N-tosylimine derivatives

Friedel-Crafts reaction of aromatic compounds with the Baylis-Hillman adducts of N-tosylimine derivatives in the presence of sulfuric acid provided a stereoselective methodology for the preparation of 2-benzylsubstituted olefins in moderate yields.

The Friedel-Crafts reaction of the Baylis-Hillman adducts

A simple and convenient methodology for the stereoselective construction of 2-benzyl substituted trisubstituted olefins via sulfuric acid catalyzed Friedel-Crafts reaction of benzene with Baylis-Hillman adducts is described.

Applications of the Baylis-Hillman Reaction 2: a Simple Stereoselective Synthesis of (E)- and (Z)-Trisubstituted Alkenes

Reaction of Grignard reagents with methyl 3-acetoxy-2-methylenealkanoates produces (2E)-2-substituted alk-2-enoates, whereas a similar reaction with 3-acetoxy-2-methylenealkanenitriles provides (2Z)-2-substituted alk-2-enenitriles in high (Z)-stereoselectivity.