2077-35-2

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 135-02-4 ortho-anisaldehyde 
• 693-03-8 n-butyl magnesium bromide 
• 66021-98-5 (o-methoxyphenyl)-1-propyne 
• 3698-28-0 2-allylanisole 
• 1066-35-9 dimethylmonochlorosilane 
• 578-57-4 2-bromoanisole 
• 24850-33-7 allyltributylstanane 
• 4736-60-1 ethyltriphenylphosphonium iodide 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 7035-02-1 o-Methoxybenzyl chloride 
• 1373402-23-3 2-methoxybenzyl(methyl)diphenylphosphonium chloride 
• 75-07-0 acetaldehyde 
• 134749-77-2 [1-(2-Methoxy-phenylmethanesulfonyl)-ethylidene]-triphenyl-λ⁵-phosphane 

Relevant academic research and scientific papers

Iron Catalyzed Double Bond Isomerization: Evidence for an FeI/FeIII Catalytic Cycle

Iron-catalyzed isomerization of alkenes is reported using an iron(II) β-diketiminate pre-catalyst. The reaction proceeds with a catalytic amount of a hydride source, such as pinacol borane (HBpin) or ammonia borane (H3N?BH3). Reactivity with both allyl arenes and aliphatic alkenes has been studied. The catalytic mechanism was investigated by a variety of means, including deuteration studies, Density Functional Theory (DFT) and Electron Paramagnetic Resonance (EPR) spectroscopy. The data obtained support a pre-catalyst activation step that gives access to an η2-coordinated alkene FeI complex, followed by oxidative addition of the alkene to give an FeIII intermediate, which then undergoes reductive elimination to allow release of the isomerization product.

Copper-catalyzed semihydrogenation of internal alkynes with molecular hydrogen

A copper-catalyzed system using a commercially available simple N-heterocyclic carbene ligand under atmospheric pressure of H2 (1 atm, balloon) enables the semihydrogenation of internal alkynes, which proceeds with high Z selectivity. Thus, this copper catalysis provides a useful method for the preparation of (Z)-alkenes from internal alkynes.

Photooxidizing chromium catalysts for promoting radical cation cycloadditions

The photooxidizing capabilities of selected CrIII complexes for promoting radical cation cycloadditions are described. These complexes have sufficiently long-lived excited states to oxidize electron-rich alkenes, thereby initiating [4+2] processes. These metal species augment the spectrum of catalysts explored in photoredox systems, as they feature unique properties that can result in differential reactivity from the more commonly employed ruthenium or iridium catalysts. Spotlight on chromium: Selected CrIII complexes were investigated for promoting radical cation cycloadditions. These species have sufficiently long-lived excited states to oxidize electron-rich alkenes, thereby initiating [4+2] processes. These metal complexes augment the spectrum of catalysts explored in photoredox systems, featuring properties that can result in differential reactivity from the more common Ru or Ir catalysts.

Photocatalytic synthesis of dihydrobenzofurans by oxidative [3+2] cycloaddition of phenols

We report a protocol for oxidative [3+2] cycloadditions of phenols and alkenes applicable to the modular synthesis of a large family of dihydrobenzofuran natural products. Visible-light-activated transition metal photocatalysis enables the use of ammonium persulfate as an easily handled benign terminal oxidant. The broad range of organic substrates that are readily oxidized by photoredox catalysis suggests that this strategy may be applicable to a variety of useful oxidative transformations.

A facile and convenient sequential homobimetallic catalytic approach towards β-methylstyrenes. A one-pot Stille cross-coupling/isomerization strategy

An efficient one-pot synthetic approach towards β-methylstyrenes is reported. The transformation, based on sequential homobimetallic catalysis, involves a Stille cross-coupling reaction between aryl halides and allyltributylstannane, followed by an in situ palladium-catalyzed conjugative isomerization. The reaction was optimized, and the best results were obtained with 10 mol% Pd(PPh3)2Cl2, 8.0 equiv. LiCl, and 0.5 equiv. PPh3 in diglyme at 130 °C for 12 h. It was demonstrated that the reaction tolerates a wide variety of functional groups. This journal is the Partner Organisations 2014.

A convenient and mild chromatography-free method for the purification of the products of Wittig and Appel reactions

A mild method for the facile removal of phosphine oxide from the crude products of Wittig and Appel reactions is described. Work-up with oxalyl chloride to generate insoluble chlorophosphonium salt (CPS) yields phosphorus-free products for a wide variety of these reactions. The CPS product can be further converted into phosphine.

Manganese(II) chloride-catalyzed alkylmagnesation of 2-alkynylphenol

Treatment of 2-alkynylphenol with an alkyl Grignard reagent in the presence of a catalytic amount of manganese(II) chloride provided 2-(2-alkyl-1-alkenyl)phenol in good yield. Alkylmagnesation proceeded with high regio-and stereoselectivities.

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 12. Extrusion of Ph3P from sulfonyl ylides and reactivity of the resulting sulfonyl carbenes

Twelve sulfonyl stabilised phosphorus ylides have been prepared and their behaviour upon flash vacuum pyrolysis at 600°C has been examined. Examples with an arylsulfonyl substituent undergo loss of Ph3PO to give intractable products but those with an arylmethylsulfonyl substituent separately lose Ph3P and SO2 to give products consistent with the intermediacy of sulfonyl carbenes. X-Ray structure determinations of one ylide from each series show a more significant P-O non-bonding interaction in the first case, providing some explanation for the different thermal reactivity.

Development of a polymer bound Wittig reaction and use in multi-step organic synthesis for the overall conversion of alcohols to β-hydroxyamines

An efficient combinatorial access to β-hydroxyamines suitable for automation is achieved by the mild oxidation of alcohols to aldehydes by polymer supported perruthenate (PSP), the subsequent clean olefination of the obtained aldehydes by polymer supported Wittig reagents followed by the epoxidation of the olefins by dimethyldioxirane (DMDO), and the final aminolysis of the epoxides with various amines is described.

Sulfonium salts and process for their preparation

The present invention provides photoactive sulfonium salts which can be employed as photoinitiators for the polymerization of cationically polymerized organic substances and are soluble in these substances.