42858-33-3

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 93-55-0 1-phenyl-propan-1-one 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 34837-55-3 Phenylselenyl bromide 
• 104755-22-8 C₁₅H₁₄Cl₂OSe 
• 42572-42-9 phenylselenium trichloride 
• 645-96-5 Benzeneselenol 
• 873-66-5 1-propenylbenzene 
• 1666-13-3 diphenyl diselenide 

Downstream Products

• 56253-60-2 trimethyl-phenylselanylmethyl-silane 
• 116333-32-5 erythro-1-Phenyl-2-(phenylseleno)propan-1-ol 
• 116333-32-5 threo-1-Phenyl-2-(phenylseleno)propan-1-ol 
• 768-03-6 Phenyl vinyl ketone 
• 93-54-9 1-Phenyl-1-propanol 
• 831200-81-8 phenyl-N-(1-phenyl-2-(phenylselanyl)propylidene)methanamine 
• 84993-33-9 C₁₆H₁₆Se 
• 1218948-27-6 C₁₈H₁₉NSe 
• 1194360-66-1 C₁₈H₁₈O₂Se 

Relevant academic research and scientific papers

Visible-light-induced oxidative coupling of vinylarenes with diselenides leading to α-aryl and α-alkyl selenomethyl ketones

A visible-light-induced oxidative coupling of diselenides with readily available vinylarenes is demonstrated. This benign protocol allows one to access a wide range of α-aryl and α-alkyl selenomethyl ketones in good yields with excellent functional group compatibility. The distinct advantages of this protocol over all previous methods include the use of a green solvent and air as an oxidant and the lack of a photocatalyst, a base, and an oxidant as well as better green chemistry matrices. Furthermore, the title reaction can be performed with natural sunlight, the most sustainable energy source imaginable. Additionally, the mild reaction conditions, easy operation and suitability for the modification of styrene-functionalized biomolecules make the current reaction system a more attractive method for the synthesis of a variety of medicinal and agrochemical compounds of interest.

N, N, N -Triphenylselenylisocyanuric Acid (TPSCA): A New Versatile Reagent for α-Phenylselenenylation of Aldehydes and Ketones

A new, versatile reagent, N,N,N-triphenylselenyl-isocyanuric acid (TPSCA) has been prepared, characterized, and used as a source of the electrophilic phenylselenyl group. This relatively stable compound was utilized for an efficient α-selenenylation react

A radical cyclization route to cyclic imines

A novel route to cyclic imines based on 5-exo radical cyclization is explored. The radical precursors are imines prepared from allylamine and readily available α-phenylselenenyl ketones.

The effects of C-S and C-Se bonds on torquoselectivity: stereoselective olefination of α-thio and α-selenoketones with ynolates

Highly Z-selective olefination of acyclic α-thio and α-selenoketones with ynolates has been achieved, and the theoretical calculations of the transition states in the ring-opening of the intermediates, the β-lactone enolates, revealed that the torquoselectivity was controlled by the secondary orbital interactions between the σ orbital of the C-S bond or a lone pair orbital on the S and σ* orbitals of the breaking C-O bond, and the σ orbital of the breaking C-O bond or a lone pair orbital on the O on the ring and the σ* orbitals of the C-S bond. The synthetic applications of the resulting olefins are also shown.

Use of phenylselenium trichloride for simple and rapid preparation of α-phenylselanyl aldehydes and ketones

α-Phenylselanyl aldehydes are prepared on a large scale by reaction of PhSeCl3 with the corresponding aldehydes in acetonitrile without isolation of the intermediate dichloro adducts. This method has been applied to α-phenylselanyl ketones deri

Stereo- and Chemo-Selectivity in reduction of α-alkyl Aryl Ketones with Metal Hydrides

Metal hydride reduction of a variety of α-alkyl aryl ketones gives a mixture of threo- and erythro-β-aryl-β-hydroxyalkyl phenyl(or methyl)selenides by carbonyl reduction and 1-aryl-1-alkanol by the substitution of a phenyl(or methyl)seleno group with hydrogen.With all metal hydrides examined the formation of the threo-isomer always predominated.The addition of various metal chlorides in the reduction of various α-heteroatom (N, P, O, S)-substituted ketones.

Preparation of 2-Arylpropanoic Acids by Oxidative Aryl Migration in (β-Aryl-β-hydroxy)alkyl Phenyl Selenides

Oxidation of diastereomeric mixtures of 1-aryl-1-hydroxyprop-2-yl phenyl selenides, prepared either by phenylselenylation of propiophenones followed by reduction or by treatment of benzaldehyde with α-(phenylseleno)ethyl anion, with an excess of meta-chloroperbenzoic acid in methanol at 25 deg C for 24 h or at reflux for 2 h affords methyl 2-arylpropanoates almost quantitatively.Similar treatment in tetrahydrofuran at 25 deg C for 24 h results in a direct formation of 2-arylpropanoic acids in high yields.

Application of Oxidative Aryl Migration in Organo-selenium and -tellurium Compounds to the Synthesis of 2-Arylpropanoic Acids

The ethylene acetals of aryl α-phenylseleno- and α-phenyltelluro-ethyl ketones i, Ph, Br) and 5-bromo-6-methoxy-2-naphthyl> have been prepared in 12-83percent yields by treating the corresponding α-bromo compounds with diphenyl diselenide-sodium or diphenyl ditelluride-sodium, respectively, in tetrahydrofuran-dimethylformamide under reflux for 6-10 h, during which the bromine is substituted by the PhSe or PhTe group.This substitution is not observed when the (PhM)2-NaBH4-EtOH (M=Se, Te) system which is known as a source of PhM- anion is used.Oxidation of the acetals thus formed with an excess of meta-chloroperbenzoic acid at 20-25 deg C for 1 h affords hydroxy-ethyl 2-arylpropanoates in 56-86percent yields via aryl group migration which are hydrolysed to 2-arylpropanoic acids, some of which are pharmaceutically important compounds.Overall isolated yields of 2-arylpropanoic acids are around 30-42percent based on the starting propiophenones over 5 steps.

Preparations de composes α-arylselenocarbonyles a l'aide de morpholinoareneselenenamides

The reactivity of the morpholinoareneselenenamides 1 which are readily prepared from various diaryldiselenides, is investigated.The selenenamides 1 are good α-selenenylating agents for aliphatic aldehydes, α-ketoesters and conjugated enals yielding the α-

New Preparative Method for 2-Arylpropanoic Acids by Oxidative Aryl Migration in Aryl α-Seleno- and Aryl α-Telluro-ethyl Ketones

Oxidation with m-chloroperbenzoic acid of the ethylene acetals of aryl α-phenylseleno- or aryl α-phenyltelluro-ethyl ketones prepared by treating the corresponding α-bromo compounds with diphenyl diselenide-sodium or diphenyl ditelluride-sodium, respectively, affords hydroxyethyl 2-arylpropanoates in moderate to good yields via aryl group migration.