54322-62-2

Upstream product

• 100-10-7 4-dimethylamino-benzaldehyde 
• 38152-43-1 C₂₄H₄₀N₂O₂Si₂ 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 100-52-7 benzaldehyde 

Downstream Products

• 1314045-00-5 1,1-di(azulen-1-yl)-2,2-bis[4-(dimethylamino)phenyl]ethylene 
• 1314044-97-7 1,1-di(azulen-1-yl)-2,2-bis[4-(dimethylamino)phenyl]ethane 
• 1314044-93-3 2-(azulen-1-yl)-1,1-bis[4-(dimethylamino)phenyl]ethylene 
• 1314044-98-8 (1R,2S)-1,2-di(azulen-1-yl)-1,2-bis[4-(dimethylamino)phenyl]ethane 
• 1314044-96-6 1,3-bis{2,2-bis[4-(dimethylamino)phenyl]ethenyl}azulene 
• 41327-20-2 1,2-bis(4-dimethylaminophenyl)ethanone 
• 80721-78-4 2,6,9,10-tetracyanoanthracene radical anion 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 17078-27-2 4,4'-bis(dimethylamino)benzil 

Relevant academic research and scientific papers

A convenient synthesis of unsymmetrical pinacols by coupling of structurally similar aromatic aldehydes mediated by low-valent titanium

The one-pot, selective cross pinacol-type couplings between two structurally similar aromatic aldehydes promoted by low-valent titanium generated unsymmetrical pinacols in moderate to good isolated yields in an erythrolthreo ratio of up to 91:9. This synt

Pinacol coupling of carbonyl compounds by using Al-NaOH/MeOH under microwave irradiation

Reductive coupling of aromatic aldehydes and ketones to the corresponding 1,2-diols has been achieved in 59-98% yields using aluminium powder in aqueous sodium hydroxide and methanol medium under microwave irradiation for 5-12 min. The notable advantage of this method seems to be negligible formation of simple amounts of reduced product of the carbonyls i.e. alcohols and the formation of side product olefins via McMurry coupling. The reaction rate is fast and the purity of products is compared to the existing methods. The potential Pinacol rearrangement of the reductive coupling products greatly extends their synthetic utility.

Novel and efficient Ni-mediated pinacol coupling of carbonyl compounds

It was firstly found that the Rieke Ni generated in situ was able to promote the pinacol coupling of various carbonyls efficiently. Based on this information, another catalytically effective, cheaper and more convenient NiCl2(Cat.)/Mg/TMSCl system was designed and developed further successfully. The interesting single-electron transfer (SET) mechanisms for the coupling reactions were proposed. Additionally, the DL/meso diastereoselectivity and some additive effects were also explained in terms of the proposed mechanisms.

Synthesis of pinacols through electrochemical reduction of carbonyl compounds at platinum cathode in non-aqueous weakly acidic medium

The electrochemical reduction of p-methylacetophenone, m-nitrobenzaldehyde p-dimethylaminobenzaldehyde and p-hydroxybenzaldehyde was carried out at controlled potential in weakly acidic medium (phenol, pKa = 9.98) for the purpose of investigating this type of reduction as a possible synthetic procedure for the preparation of 1,2-diol (or pinacol). The products formed during electrolysis at constant cathode potential are reported here.

Alkylative Reduction of Titanium(IV) Isopropoxide with EtMgBr: Convenient Method for the Generation of Subvalent Titanium Alkoxide Reagents and their Reactivity in Pinacol Coupling Reactions

The composition of the gaseous products from the reaction of Ti(IV) isopropoxide with ethylmagnesium bromide in diethyl ether evidences the formation of subvalent titanium isopropoxide species in various oxidation states depending on relative amounts of the reactants. Reaction of titanium(IV) isopropoxide with one equivalent of the Grignard reagent gives presumably titanium(III) isopropoxide. The latter is generated as a result of disproportionation of starting Ti(IV) species and titanium(II) isopropoxide-ethene complex which is formed as a result of ethane extrusion from diethyltitanium(IV) isopropoxide. Titanium(III) isopropoxide prepared by this way transforms the aldehydes and the aromatic ketones into the corresponding pinacols in good yields.

Photoinduced electron transfer retropinacol reaction of 4-(N,N-dimethylamino)phenyl pinacols in chloroform

UV irradiation of 1,2-bis[4-N,N-(dimethylamino)phenyl]ethane-1,2-diol (1a) and 2,3-bis[4-(N,N-dimethylamino)phenyl]butane-2,3-diol (1b) in deaerated chloroform leads to central carbon-carbon bond cleavage (retropinacol reaction) forming 4-(N,N-dimethylami

Photochemical Electron Transfer Initiated Oxidative Fragmentation of Aminopinacols. Factors Governing Reaction Rates and Quantum Efficiencies of C-C Bond Cleavage

The fragmentation reactions of the cation radicals of a series of remote diamine-substituted pinacols have been investigated.The cation radicals were generated upon photooxidation with excited 2,6,9,10-tetracyanoanthracence in acetonitrile.The products are consistent with cleavage of the central C-C bond.The rate constants for fragmentation were determined both from steady-state quantum yield studies and from time-resolved measurements.In general, the rate constants for fragmentation increase with increasing stability of the radical and cation products.However, the results of temperature dependence studies clearly demonstrate that conformational effects play an important role in the transition state.In some cases, these conformational effects can result in changes in the reactivity order expected from purely thermodynamic considerations.

Generation of Metal-Free Silyl Anions from Disilanes and Fluoride Catalyst. Synthetic Reactions with Aldehydes and 1,3-Dienes

The Si-Si bond of disilanes is found to be cleaved by tetrabutylammonium fluoride (TBAF) in hexamethylphosphoric triamide to produce metal-free silylanion and triorganosilyl fluoride.The disilane/TBAF reagent was studied spectrometrically.Sythetic application of the reagent with a catalytic amount of TBAF is illustrated by the reaction with aldehydes and 1,3-dienes.

EFFICIENT FORMATION OF PINACOLS FROM ALDEHYDES OR KETONES MEDIATED BY SAMARIUM DIIODIDE

Samarium diiodide is an excellent reagent for aldehyde or ketone coupling.With aromatic aldehydes, reactions are very fast with a complete selectivity versus substituents such as cyano, carbonyl or nitro groups.

SOME ORGANIC REACTIONS PROMOTED BY SAMARIUM DIIODIDE

Various homoallylic alcohols and homobenzylic alcohols were prepared by the reaction between aldehydes and allylic or benzylic halides in the presence of samarium diiodide.This iodide is also a very good reagent for formation of pinacols from aldehydes or ketones.The reactions are especially fast and selective in the case of substituted benzaldehydes.The reactivities of various nitrogen functional groups (imine, oxime, nitro, azo, cyano) towards SmI2 were also examined.