115872-74-7

Upstream product

• 6908-73-2 (E)-1-styrylpyrrolidine 
• 122-78-1 phenylacetaldehyde 
• 1866-31-5 (E)-allyl cinnamate 
• 100-52-7 benzaldehyde 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 100-42-5 styrene 
• 20780-53-4 (R)-Styrene oxide 
• 65-85-0 benzoic acid 
• 841-76-9 triphenylaluminium 

Downstream Products

• 15811-37-7 1,2,4-triphenyl-1H-pyrrole 

Relevant academic research and scientific papers

Synthesis of Multisubstituted Pyrroles from Enolizable Aldehydes and Primary Amines Promoted by Iodine

1,2,4-Trisubstituted pyrroles were synthesized from enolizable aliphatic aldehydes and primary aliphatic amines by using iodine as the dual Lewis acid/mild oxidant. In the presence of 3.0 equiv of TBHP, enolizable α,β-unsaturated aldehyde, for example, co

Tandem Acid/Pd-Catalyzed Reductive Rearrangement of Glycol Derivatives

Herein, we describe the acid/Pd-tandem-catalyzed transformation of glycol derivatives into terminal formic esters. Mechanistic investigations show that the substrate undergoes rearrangement to an aldehyde under [1,2] hydrogen migration and cleavage of an oxygen-based leaving group. The leaving group is trapped as its formic ester, and the aldehyde is reduced and subsequently esterified to a formate. Whereas the rearrangement to the aldehyde is catalyzed by sulfonic acids, the reduction step requires a unique catalyst system comprising a PdII or Pd0 precursor in loadings as low as 0.75 mol % and α,α′-bis(di-tert-butylphosphino)-o-xylene as ligand. The reduction step makes use of formic acid as an easy-to-handle transfer reductant. The substrate scope of the transformation encompasses both aromatic and aliphatic substrates and a variety of leaving groups.

Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides

The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides, ring opening occurs selectively at terminal positions, and stereocenters of epoxides are fully retained. Mechanistic studies provide evidence for in situ conversion of epoxides to β-halohydrins, generation of alkyl radicals, and radical addition to alkenes as key steps. Cyclovoltammetric determination of reduction potentials suggests that during activation of alkyl iodides by palladium(0) complexes, inner-sphere halogen abstraction is more likely than outer-sphere single electron transfer.

Tandem nucleophilic addition-Oppenauer oxidation of aromatic aldehydes to aryl ketones with triorganoaluminium reagents

In the presence of pinacolone, the in situ prepared triorganoaluminium reagents reacted with aromatic aldehydes to give ketones in moderate to high yield. We propose that the products are formed via a tandem organoaluminium reagents addition-Oppenauer oxidation sequence. The Royal Society of Chemistry 2013.

Studies on the Oxidation of Enamines with Molecular Oxygen. III Oxidation of Some Amino Styrenes

In the oxidation of the amino styrenes 1a - 1j only products of the oxidative attack at the C=C double bond and hydrolysis products are obtained.Aprotic dipolar solvents and the addition of molecular sieve 5A promote the oxygen uptake.The addition of hydroquinone to the oxidation system does not influence the rate of oxygen absorption or the yields of the oxidation products.

A Regiocontrolled Synthesis of Allylstannanes

β-Stannyl ester enolates react with aldehydes with fairly high stereoselectivity, the isomeric enolates (4) and (2) respectively giving as major products the allyl hydroxy-stannylbutanoates (6) and (7) with opposite aldol relative stereochemistry.These aldols can be converted stereospecifically (steric and reactivity effects allowing) into the allylstannanes (13) and (14).The cis allylstannane (14aa) is stable to isomerisation in non-polar solvents.