1846-19-1

Upstream product

• 123-06-8 Ethoxymethylenemalononitrile 
• 2700-22-3 Benzylidenemalononitrile 
• 10394-96-4 2-(diphenylmethylene)malononitrile 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 853-83-8 N-tosyldiphenylmethylamine 
• 109-77-3 malononitrile 
• 1013-88-3 Benzophenone imine 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 91-01-0 1,1-Diphenylmethanol 
• 100-52-7 benzaldehyde 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 10394-96-4 2-(diphenylmethylene)malononitrile 

Relevant academic research and scientific papers

Reduction of activated olefins by SmI2. Detouring the classical birch mechanism and a negative order in SmI2

The reaction of an excess of 1,1-diaryl-2,2-dicyanoethylenes (1) with SmI2 is biphasic for olefin with at least one available para position. The first phase is completed in less than 0.5 s with the second phase extending over a few hundred seco

AlCl3 catalyzed coupling of: N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon-nitrogen bond cleavage

A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.

An efficient greener copper triflate-catalyzed C-3 benzylation of 4-hydroxycoumarin and some active methylene compounds

4-Hydroxycoumarin has been directly benzylated at C-3 position with a good number of secondary benzylic alcohols using copper triflate catalyst (2 mol%) in toluene under reflux. The protocol provides an efficient, expedient and atom-economic access to warfarin and coumatetralyl analogues with potential anticoagulant activity. The protocol has been extended to benzylation of 4-hydroxy-1-methylquinolin-2(1H)-1-one, N-methylbarbiturate and some other active methylene compounds with remarkable success.

Facile metal free regioselective transfer hydrogenation of polarized olefins with ammonia borane

Transfer hydrogenation of polarized olefins bearing strongly electron-withdrawing groups on one side of the double bond was achieved with ammonia borane under mild conditions without using a catalyst. Mechanistic studies proved the character of the direct H transfers proceeding stepwise with a unique hydroboration intermediate and hydride before proton transfer.

Copper-catalyzed 1,4-addition of organoboronates to alkylidene cyanoacetates: Mechanistic insight and application to asymmetric catalysis

In addition: A copper/N-heterocyclic carbene(NHC)-catalyzed 1,4-addition of organoboronates to alkylidene cyanoacetates was developed, in which the catalytic cycle is proposed to consist of a transmetalation/insertion/ligand exchange. An effective asymmetric variant has also been achieved by the use of a chiral NHC ligand (see scheme). Copyright

Polymer-supported hantzsch 1,4-dihydropyridine ester: An efficient biomimetic hydrogen source for the reduction of ketimines and electron-withdrawing group conjugated olefins

A polymer-supported Hantzsch 1,4-dihydropyridine ester was observed to be a useful selective reducing agent for the reduction of ketimines and electron-withdrawing conjugated olefins. The rate of the reduction of electron-withdrawing conjugated olefins is dependent on the nature of the conjugated substituents and could be enhanced by microwave irradiation. The reduction of (Z)-α-cyano-β-bromomethylcinnamates to cyclopropane derivatives using polymer-supported Hantzsch 1,4-dihydropyridine ester was found to proceed stereoselectively and in good yields.

Selective benzylic and allylic alkylation of protic nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp3 carbon-nitrogen bonds

The acid-catalyzed benzylic and allylic alkylation of protic nucleophiles is fundamentally important for the formation of carbon-carbon and carbon-heteroatom bonds, and it is a formidable challenge for benzylic and allylic amine derivatives to be used as the alkylating agents. Herein we report a highly efficient benzylic and allylic alkylation of protic carbon and sulfur nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp3 carbon-nitrogen bonds at room temperature. In the presence of a catalytic amount of inexpensive ZnCl2-TMSCl (TMSCl: chlorotrimethylsilane), 1,3-diketones, β-keto esters, β-keto amides, malononitrile, aromatic compounds, thiols, and thioacetic acid can couple with a broad range of tosylactivated benzylic and allylic amines to give diversely functionalized products in good to excellent yields and with high regioselectivity. Furthermore, the cross-coupling reaction of 1,3-dicarbonyl compounds with benzylic propargylic amine derivatives has been successfully applied to the one-step synthesis of polysubstituted furans and benzofurans.

A study on the reactions of NADH models with electron-deficient alkenes. A probe for the extreme of concerted electron-hydrogen atom transfer mechanism

The reactions of 9-fluorenylidenemalononitrile (FDCN) and 1,1-diphenyl-2,2-dicyanoethylene (DPCN) with Hantzsch ester (HEH), N-methyl Hantzsch ester (Me-HEH), and 1-benzyl-1,4-dihydronicotinamide (BNAH) in oxygen-saturated acetonitrile have been studied. The aerobic reactions with HEH give solely reduction products. However, reactions with Me-HEH and BNAH not only result in reduction products, but also give varying amounts of oxidation products. The amount of oxidation product appears to be related to the electronic character and bulkiness of reactants. We propose that all these reactions follow a general mechanism of concerted electron-hydrogen atom transfer mechanism. If the electron-transfer complex is very tight, only 'concerted hydride transfer reaction' occurs. However, if the electron-transfer complex is not so tight, oxygen can capture the radicaloid intermediate to result in oxidation products.

Cyclodimerization of 1,1-dicyanoalkenes and arylidenecyanoacetates promoted by ytterbium diiodide

The reductive cyclodimerization of 1,1-dicyanoalkenes and arylidenecyanoacetates promoted by Ybl2 has been studied. Functionalized cyclopentenes are obtained in both high yields and stereoselectivity.