4285-51-2

Upstream product

• 821-09-0 n-Pent-4-enyl alcohol 
• 3111-52-2 potassium thiophenolate 
• 74-86-2 acetylene 
• 82239-64-3 pent-1-yn-5-yl phenyl sulfide 
• 1119-51-3 bromopentene 
• 108-98-5 thiophenol 
• 1795-09-1 2-methylthiolane 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Downstream Products

• 57774-95-5 5-(phenylthio)-1-pentanol 
• 83705-76-4 5-(phenylthio)-1-iodopentane 
• 182140-48-3 [Pd(Br)(C₆H₅SC₂H₄CHC₂H₄C₆F₅)]2 
• 144121-60-8 1-phenylhex-5-en-1-ol 
• 41795-36-2 5-(phenylsulfonyl)-1-pentene 

Relevant academic research and scientific papers

Synthesis of α-Cyano and α-Sulfonyl Cyclic Ethers via Intramolecular Reactions of Peroxides with Sulfone- And Nitrile-Stabilized Carbanions

The intramolecular reaction of carbon nucleophiles with oxygen-centered electrophiles has been little explored outside of nucleophilic epoxidation. We now report the synthesis of sulfonyl- and cyano-substituted oxacycles via intramolecular reaction of sul

An aryne triggered ring-opening fluorination of cyclic thioethers with potassium fluoride

Herein, we report an aryne triggered ring-opening fluorination protocol of a great variety of saturated sulfur heterocycles. A key factor for the success is the identification of a suitable mediator. Compared to previous methods, this transition-metal free protocol employs low-cost potassium fluoride as the fluorine source. The operational simplicity and mild reaction conditions allow for the rapid synthesis of a wide range of aliphatic fluoride compounds in good yields.

Synergetic Effect of Monomer Functional Group Coordination in Catalytic Insertion Polymerization

PhS- and PhNH-functionalized dienes are copolymerized efficiently with butadiene to stereoregular copolymers by [(mesitylene)Ni(allyl)][BArF4] (Ni-1). Overall polymerization rates and comonomer incorporations depend strongly on the l

Regioselective Alkoxycarbonylation of Allyl Phenyl Ethers Catalyzed by Pd/dppb under Syngas Conditions

A simple and regioselective synthesis of phenoxy esters and phenylthio esters is reported. The products are obtained by selective alkoxycarbonylation catalyzed by Pd2(dba)3, 1,4-bis(diphenylphisphino)butane (dppb), and syngas (CO/H2) in chloroform/alcohol. This methodology affords bifunctional products in good yield with excellent n-selectivity and without the need to use additives.

A practical and chemoselective Mo-catalysed sulfoxide reduction protocol using a 3-mercaptopropyl-functionalized silica gel (MPS)

A convenient sulfoxide deoxygenation procedure using a mercaptopropyl-functionalized silica gel as the reducing agent is described. This new protocol based on a heterogeneous reagent displays broad scope and tolerance to reducible functional groups and, from an experimental point of view, enhances previous methods by simplifying the isolation of the sulfide to a simple filtration.

Reductive Lithiation in the Absence of Aromatic Electron Carriers. A Steric Effect Manifested on the Surface of Lithium Metal Leads to a Difference in Relative Reactivity Depending on Whether the Aromatic Electron Carrier Is Present or Absent

One of the most widely used methods of preparation of organolithium compounds is by the reductive lithiation of alkyl phenyl thioethers or, usually less conveniently, alkyl halides with either aromatic radical-anions of lithium or lithium metal in the presence of an aromatic electron-transfer catalyst. Here we present results showing that lithium dispersion can achieve reductive lithiation in the absence of the electron-transfer agent. This procedure is more efficient, and surprisingly, the order of reactivity of substrates is reversed depending on whether the electron-transfer agent is present or absent. For example, in the presence of a preformed radical-anion, tert-butyl phenyl sulfide cleaves significantly faster than methyl phenyl sulfide, whereas in the absence of the radical-anion, it is just the opposite. Density functional theory calculations reveal that the exothermicity of the cleavage of the C-S bond in alkyl phenyl thioethers on the lithium surface is dependent on the size of the alkyl group, the smaller the alkyl group the greater the exothermicity. The increased reactivity is attributed to the smaller steric repulsion between the alkyl group and the lithium surface. The methodology includes, but may not be limited to, the lithium dispersion reductive lithiation of phenyl thioethers, alkyl chlorides, acrolein diethyl acetal, and isochroman.

An unprecedented use for glycerol: Chemoselective reducing agent for sulfoxides

A new application for glycerol that expands its possibilities beyond a green solvent and a precursor of value-added products has been demonstrated. Simple, easily available, and environmentally friendly dioxomolybdenum(vi) complexes are highly efficient catalysts for the chemoselective sulfoxide deoxygenation with this biomass-derived chemical feedstock. Both refined glycerol and crude glycerin can be used, thus expanding the potential application of this reaction. Subsequent transformation of glycerol during this reductive process has also been investigated.

Pinacol as a new green reducing agent: Molybdenum-catalyzed chemoselective reduction of sulfoxides and nitroaromatics

Pinacol is disclosed as a new chemoselective and environmentally benign reducing agent for sulfoxides and nitroaromatics assisted by readily available dichlorodioxomolybdenum(VI) complexes as catalysts. A wide range of substrates including those bearing challenging functional groups has been efficiently and selectively reduced with acetone and water being the only by-products of these reactions. Copyright

Antarafacial mediation of oxygen delivery by a phenylsulfinyl group in the epoxidation of proximal double bonds: Intramolecular trapping of an early Pummerer intermediate with stereoelectronic control

Stereospecific intramolecular antarafacial epoxidation of a double bond via an early Pummerer reaction intermediate has been demonstrated. The intermediate is presumably generated via trifluoroacetylation of a sulfoxide precursor. Ionization of trifluoroa