3320-35-2

Upstream product

• 5653-29-2 2-(1,3-dithiolan-2-yl)-1-phenylethan-1-one 
• 104-53-0 3-phenyl-propionaldehyde 
• 624-31-7 4-tolyl iodide 
• 14371-10-9 (E)-3-phenylpropenal 
• 88445-16-3 1-(4-methylphenyl)-1-phenyl-2-propyn-1-ol 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 126838-29-7 ethyl 3-(4-methylphenyl)-3-phenyl-2-propenoate 
• 5720-05-8 4-methylphenylboronic acid 
• 350831-23-1 1,1,4-triphenyl-4-p-tolyl-but-3-ene-1,2-diol 
• 104-55-2 3-phenyl-propenal 
• 134-84-9 4-Methylbenzophenone 
• 121-44-8 triethylamine 
• 106-38-7 para-bromotoluene 
• 350831-07-1 (dimethyl-p-tolylethynyl-silanyloxy)-diphenyl-acetaldehyde 

Downstream Products

• 92804-29-0 3-phenyl-3-(4-methylphenyl)propanal 

Relevant academic research and scientific papers

[PF6]2 As catalyst for the meyer-schuster rearrangement of arylpropargylic alcohols under mild conditions

The novel iridium complex [IrCpNCMe2PPh2Me][PF6]2 I efficiently catalyzed the Meyer-Schuster rearrangement of selected arylpropargylic alcohols into α,β-unsaturated aldehydes under mild conditions and without the need of a co-catalyst. A mechanism involving a hydroxy alkenylcarbene intermediate is proposed. [IrCpNCMe2PPh2Me][PF6]2 efficiently catalyzes the rearrangement of propargylic alcohols into α,β-unsaturated aldehydes under mild conditions and without the need of a co-catalyst.

Mizoroki–Heck reaction of 1,2-disubstituted aryl alkenes: Variables of synthesis, solvent and ligand modulation of reactivity

Reaction of aryl iodides with 1,2-disubstituted aryl alkenes in the presence of TBABr/TBACl gave high yields of the Mizoroki–Heck product. Phosphine ligands were used for the modulation of reactivity and stereoselectivity, for the reaction of 4-iodoanisole with cinnamaldehyde. tert-Bu3P.HBF4 gave the highest E:Z ratio of 1:0.08. The use of PEG-200 and PEG-400 as solvent could activate the reaction of aryl iodides with various 1,2-disubstituetd aryl alkenes.

Silver sequestration of halides for the activation of Pd(OAc)2 catalyzed Mizoroki-Heck reaction of 1,1 and 1,2 - Disubstituted alkenes

A ligand free catalytic system consisting of Pd(OAc)2 (cat) and stoichiometric quantities of silver salts, AgOAc or AgBF4, exhibit high efficiency in the Mizoroki-Heck arylation, transforming aryl iodides and 1,1 as well as 1,2 disubstituted alkenes into 1,1,2 – trisubstituted aryl alkenes in excellent yields in very short reaction times.

Palladium-Catalyzed Cascade Saegusa–Heck Reaction: Synthesis of β,β-Diarylacroleins from Arylpropanals and Aryl Iodides

An efficient and convenient Pd-catalyzed Saegusa–Heck cascade protocol was developed, and its potential use in the synthesis of symmetrical and unsymmetrical β,β-diarylacroleins in moderate to high yields was investigated.

A Weinreb Amide Based Building Block for Convenient Access to β,β-Diarylacroleins: Synthesis of 3-Arylindanones

Towards the synthesis of symmetrical and unsymmetrical β,β-diarylacroleins for assembling diarylmethine fragments present in biologically important molecules, we have developed a new Weinreb amide (WA) based building block, derived from propiolic acid. The WA functionality present in this compound allowed the sequential addition of various arylmagnesium bromide reagents in a controlled manner. The developed methodology for the access to β,β-diarylacroleins has been utilised for the synthesis of biologically important 3-arylindanone molecules. Synthesis of both symmetrical and unsymmetrical β,β-diarylacrolein and diarylmethine fragments, have been achieved via easily accessible and hitherto unknown Weinreb Amide (WA) based building block 11. The WA functionality allowed the sequential addition of nucleophiles such as arylmagnesium bromide in a controlled manner, which has enabled the synthesis of an important 3-arylindanone molecule.

Chiral dihydrobenzo[1,4]oxazines as catalysts for the asymmetric transfer-hydrogenation of α,β-unsaturated aldehydes

A new class of organocatalysts based on the structure of 2,3-dihydrobenzo[1,4]oxazine was prepared and applied in the enantioselective transfer-hydrogenation of α,β-unsaturated aldehydes with Hantzsch ester as hydride donor. These catalysts proved to be particularly effective for the conjugate reduction of β,β-diaryl-substituted acrylaldehydes leading to saturated aldehydes bearing a stereogenic center with two different aryl groups with enantioselectivities of up to 91% ee.

The Heck arylation of mono- and disubstituted olefins catalyzed by palladium supported on alumina-based oxides

Palladium catalysts containing Pd(0) or Pd(II) supported on alumina-based mixed oxides prepared by alkoxide sol-gel method (Al2O3, Al2O3-ZrO2, Al2O3- ZrO2-Eu2O3, Al2O3-MgO, Al2O3-CeO2, Al2O3-Fe 2O3) are very effective in the Heck coupling of bromobenzene with butyl acrylate in DMF solvent. In the presence of an excess of bromobenzene, butyl cinnamate (1) was formed as the main product after 4 h. With the same catalysts, good results, up to 97% yield of ethyl β-phenylcinnamate (3), were also obtained in the coupling of bromobenzene with ethyl cinnamate. The three most active catalysts, Pd(0)/Al 2O3, Pd(II)/Al2O3, and Pd(II)/Al2O3-Fe2O3, were applied in the Heck cross-coupling of cinnamates with different bromobenzene and iodobenzene derivatives, leading to β-arylcinnamate products. The highest yield was observed when iodoanisole and cinnamic aldehyde were used as substrates. The formation of Pd(0) nanoparticles in the Heck reaction carried out with supported Pd(II) catalyst precursors was confirmed by TEM measurements.

Nickel-catalyzed preparation of stereodefined allylic alcohols using silicon-tethered ynals

The nickel-catalyzed cyclization of silicon-tethered ynals is reported. The silicon heterocycles obtained may be converted into allylic alcohols that possess a stereodefined alkene unit via a cleavage process that involves stereospecific protodesilylation of the vinyl silane functionality.

Metalation of iminium ions formed in the reaction of tertiary amines with TiCl4

(equation presented) TiCl4 reacts with trialkylamines at 0-25°C to give iminium ions that on metalation followed by reaction with diaryl ketones, produce α,β-unsaturated aldehydes.