4285-49-8

Upstream product

• 5162-44-7 1-bromo-4-butene 
• 108-98-5 thiophenol 
• 75-11-6 diiodomethane 
• 5296-64-0 allyl phenyl thioether 
• 40671-34-9 4-methanesulfonyloxy-1-butene 
• 930-69-8 sodium thiophenolate 
• 3561-67-9 bis(phenylthio)methane 
• 762-72-1 allyl-trimethyl-silane 
• 14660-38-9 Δ³-butenylmercury chloride 
• 106-99-0 buta-1,3-diene 
• 1616562-91-4 (2-azidoallyl)(phenyl)sulfane 
• 5651-88-7 phenyl propargyl sulfide 
• 110-01-0 thiophene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Downstream Products

• 82135-75-9 phenylmethyl(3-butenyl)sulfonium fluoroborate 
• 36195-56-9 (E)-but-2-en-1-yl phenyl sulfide 
• 83180-93-2 (1-Chloro-but-3-enylsulfanyl)-benzene 
• 82135-79-3 phenylisopropyl(3-butenyl)sulfonium tetraphenylborate 
• 5296-64-0 allyl phenyl thioether 
• 874-79-3 phenyl(propyl)sulfide 
• 1126-80-3 (n-butylthio)benzene 
• 702-04-5 crotyl phenyl sulfide 
• 10276-04-7 3-methyl-1-phenylsulfanylbut-2-ene 
• 13910-11-7 3-methylbutyl phenyl sulfide 
• 22103-05-5 1-(phenylthio)-1-propene 
• 108-98-5 thiophenol 
• 182140-23-4 [Pd(Br)(C₆H₅SC₂H₄CHCH₂C₆F₅)]2 
• 1256168-95-2 1-(2-hydroxy-5-methoxyphenyl)-2-methyl-4-(phenylthio)butan-1-one 

Relevant academic research and scientific papers

A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent

A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.

Preparation of Functionalized α,β-Unsaturated Sulfonamides via Olefin Cross-Metathesis

The synthesis of functionalized α,β-unsaturated sulfonamides by means of cross-metathesis of vinyl sulfonamides and olefins has been developed. The reaction proceeds smoothly in the presence of Hoveyda-Grubbs catalyst and its nitro analogue, providing a w

Catalytic Hydrothiolation: Counterion-Controlled Regioselectivity

In this Article, we expand upon the catalytic hydrothiolation of 1,3-dienes to afford either allylic or homoallylic sulfides with high regiocontrol. Mechanistic studies support a pathway in which regioselectivity is dictated by the choice of counterion associated with the Rh center. Non-coordinating counterions, such as SbF6-, allow for η4-diene coordination to Rh complexes and result in allylic sulfides. In contrast, coordinating counterions, such as Cl-, favor neutral Rh complexes in which the diene binds η2 to afford homoallylic sulfides. We propose mechanisms that rationalize a fractional dependence on thiol for the 1,2-Markovnikov hydrothiolation while accounting for an inverse dependence on thiol in the 3,4-anti-Markovnikov pathway. Through the hydrothiolation of an essential oil (β-farnesene), we achieve the first enantioselective synthesis of (-)-agelasidine A.

Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex

We report the development of a new aminoxyl radical catalyst, CHAMPO, for the electrochemical diazidation of alkenes. Mediated by an anodically generated charge-transfer complex in the form of CHAMPO-N3, radical diazidation was achieved across a broad scope of alkenes without the need for a transition metal catalyst or a chemical oxidant. Mechanistic data support a dual catalytic role for the aminoxyl serving as both a single-electron oxidant and a radical group transfer agent.

Interruption of Formal Schmidt Rearrangement/Hosomi-Sakurai Reaction of Vinyl Azides with Allyl/Propargylsilanes

An interrupted Schmidt rearrangement/Hosomi-Sakurai reaction of N-tosyl and S-substituted vinyl azides is reported. With BF3·Et2O as a Lewis acid promoter, the denitrogenative fragmentation of vinyl azides facilitates the generation of the N/S-stabilized carbocations, which further undergo nucleophilic addition by allyl/propargylsilanes for C-C bond formation. As a result, a variety of homoallylic/allenylic amines can be afforded in good yields under mild reaction conditions with well-defined functional-group tolerance.

Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides

The preparation of chiral pool-derived nitrone 3 and its use in the protecting-group free, stereoselective synthesis of a range of 1,3-disubstituted tetrahydroisoquinolines is described. Grignard reagent additions to nitrone 3 yielded trans-1,3-disubstituted N-hydroxytetrahydroisoquinolines 6 with good levels of selectivity, while 1,3-dipolar cycloadditions to this nitrone provided access to 3-(2-hydroxyalkyl)isoquinolines 12 as single diastereomers.

Electrochemical Azidooxygenation of Alkenes Mediated by a TEMPO-N3 Charge-Transfer Complex

We report a mild and efficient electrochemical protocol to access a variety of vicinally C-O and C-N difunctionalized compounds from simple alkenes. Detailed mechanistic studies revealed a distinct reaction pathway from those previously reported for TEMPO-mediated reactions. In this mechanism, electrochemically generated oxoammonium ion facilitates the formation of azidyl radical via a charge-transfer complex with azide, TEMPO-N3. DFT calculations together with spectroscopic characterization provided a tentative structural assignment of this charge-transfer complex. Kinetic and kinetic isotopic effect studies revealed that reversible dissociation of TEMPO-N3 into TEMPO- and azidyl precedes the addition of these radicals across the alkene in the rate-determining step. The resulting azidooxygenated product could then be easily manipulated for further synthetic elaborations. The discovery of this new reaction pathway mediated by the TEMPO+/TEMPO- redox couple may expand the scope of aminoxyl radical chemistry in synthetic contexts.

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

Electrochemical Properties and Reactions of Sulfur-Containing Organoboron Compounds

Electrochemical analyses of 4,4,5,5-tetramethyl-2-phenylsulfanylmethyl-[1,3,2]dioxaborolane and tetra-n-butylammonium phenylthiomethyltrifluoroborate were comparatively studied by cyclic voltammetry measurements and we found for the first time the β-effect of organoborate, which was indicated by experimental and theoretical aspects. The organoborate was found to have a much lower oxidation potential compared to the organoborane. Anodic substitution reaction of organoboronate ester and organoborate was successfully carried out in the presence of nucleophiles to afford the selectively substituted products in good yields.

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.