20414-99-7

Upstream product

• 104722-33-0 N-acetyl, N-phenyl methyl-3 phenyl-5 amino-2 pentene-3 E 
• 497-03-0 2-methylbut-2-enal 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 100-42-5 styrene 
• 3017-68-3 (Z)-2-Bromo-2-butene 
• 108-86-1 bromobenzene 
• 4549-74-0 3-methyl-1,3-pentadiene 
• 75927-49-0 pinacol vinylboronate 
• 104722-55-6 3-Methyl-4-phenylamino-pent-1-en-3-ol 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 42599-24-6 E-styryl iodide 
• 28944-85-6 1-methyl-(Z)-propenyllithium 
• 2787-43-1 (3E)-3-methylpenta-1,3-diene 
• 110-91-8 morpholine 

Downstream Products

• 1557277-99-2 1-(5-phenylfuran-3-yl)ethanol 

Relevant academic research and scientific papers

Ligand-Free Iron-Catalyzed Carbon(sp2)-Carbon(sp2) Cross-Coupling of Alkenyllithium with Vinyl Halides

An efficient ligand-free iron-catalyzed cross-coupling reaction involving alkenyllithium and vinyl iodides was developed to form diene species in moderate to good yields. This new iron-catalyzed cross-coupling reaction provides a mild, inexpensive, and environmentally friendly avenue toward synthesis of diversified diene derivatives.

Ene-diene transmissive cycloaddition reactions with singlet oxygen: The vinylogous gem effect and its use for polyoxyfunctionalization of dienes

The singlet oxygen reactivities and regioselectivities of the model compounds 1b-d were compared with those of the geminal (gem) selectivity model ethyl tiglate (1a). The kinetic cis effect is kE/kZ = 5.2 for the tiglate/angelate system 1a/1a′ without a change in the high gem regioselectivity. Further conjugation to vinyl groups enabled mode-selective processes, namely, [4 + 2] cycloadditions versus ene reactions. The site-specific effects of methylation on the mode selectivity and the regioselectivity of the ene reaction were studied for dienes 1e-g. A vinylogous gem effect was observed for the γ,δ-dimethylated and α,γ,δ-trimethylated substrates 1h and 1i, respectively. The corresponding phenylated substrates 1j-l showed similar mode selectivity, as monomethylated 1j exhibited exclusively [4 + 2] reactivity while the tandem products 12 and 14 were isolated from the di- and trimethylated substrates 1k and 1l, respectively. The vinylogous gem effect favors the formation of 1,3-dienes from the substrates, and thus, secondary singlet oxygen addition was observed to give hydroperoxy-1,2-dioxenes 19 and 20 in an ene-diene transmissive cycloaddition sequence. These products were reduced to give alcohols (16, 17, and 18) or furans (24 and 25), respectively, or treated with titanium(IV) alkoxides to give the epoxy alcohols 26 and 27. The vinylogous gem effect is rationalized by DFT calculations showing that biradicals are the low-energy intermediates and that no reaction path bifurcations compete.

Chemoselective construction of substituted conjugated dienes using an olefin cross-metathesis protocol

(Chemical Equation Presented) Various substituted conjugated dienes have been made by olefin cross-metathesis. Using either electronic or steric "protection," one of the olefins of the conjugated diene was deactivated relative to the other for cross-metathesis. The reactions proceed with very high chemoselectivity and, when steric deactivation is used, very high diastereoselectivity.

A versatile catalyst for heck reactions of aryl chlorides and aryl bromides under mild conditions

In the presence of Cy2NMe, Pd/P(t-Bu)3 serves as an exceptionally mild and versatile catalyst for Heck reactions of aryl chlorides and bromides. A sterically and electronically diverse array of aryl bromides, as well as activated aryl chlorides, couple with a range of mono- and disubstituted olefins at room temperature, furnishing the arylated product with high E/Z stereoselection. The corresponding reactions of a broad spectrum of electron-neutral and electron-rich aryl chlorides proceed at elevated temperature, also with high selectivity. In terms of scope and mildness, Pd/P(t-Bu)3/Cy2NMe represents an advance over previously reported catalysts for these Heck coupling processes.

Regioselective 1,4-addition of ammonia to 1-arylalka-1,3-dienes and 1-aryl-4-phenylbuta-1,3-dienes by photoinduced electron transfer

The photoamination of 1-arylalka-1,3-dienes 1a-f and 1-aryl-4-phenylbuta-1,3-dienes 1g-k with NH3 in the presence of p-dicyanobenzene (DCB) gives 4-amino-1-arylalk-2-enes 2a-f and 1-amino-1,4-diarylbut-2-enes 2g-k, respectively. The photoamination proceeds by nucleophilic addition of NH3 to the cation radicals of 1+. generated by photoinduced electron transfer to DCB. The regiochemistry of 2 is related to the distribution of the positive charge in 1+. calculated by the PM3-UHF/RHF method, the stability of the aminated radicals formed by the addition of NH3 to 1+. and the stability of the aminated anion formed by the reduction of the aminated radicals by DCB-.. The stabilities of these intermediates are estimated by the calculation of the heat of formation by the PM3-UHF/RHF method. Distributions of the positive charge in 1+. and the stabilities of the aminated anion show a good agreement with the product analysis.

OBTENTION DE DERIVES ARYL BUTADIENIQUES, ORTHO AMINES OU NON, PAR COUPURE CARBONE-AZOTE, EN MILIEU BASIQUE FORT

Eliminative C-N cleavages are observed upon treatment of 2,5-dihydro-1H-1-benzazepines, of their linear analogs 4-phenyl-1-phenylamino-2-butenes and of 2,3-dihydro-1H-1-benzazepines, in the presence of strong bases (BuLi, NaNH2, t-BuOK).Thus, 16-arylbutad

Reactions of ?-Allylic Palladium Intermediates with Amines

Several dimeric ?-allylic palladium chloride complexes have been prepared by addition of aryl-, hydrido-, and (carbomethoxy)palladium chlorides, prepared in situ, to various conjugated dienes.Stoichiometric reactions of several of these complexes with secondary amines were carried out and the influence of added ligands and changes in the anions in the complexes on the reactions were noted.The stoichiometric reactions were then compared to similar catalytic reactions.The evidence suggests that the products formed in the palladium-catalyzed reactions of aryl iodides and bromides with conjugated dienes and secondary amines to form arylated dienes and allylic amines involve ?-allylic palladium complexes as intermediates.