152959-29-0

Upstream product

• 599-70-2 ethyl phenyl sulfone 
• 100-44-7 benzyl chloride 
• 62252-49-7 phenyl<(phenyl-1)propyl-2> thio-ether 
• 882-33-7 diphenyldisulfane 
• 72568-90-2 (E)-((1-phenylprop-1-en-2-yl)sulfonyl)benzene 
• 100-52-7 benzaldehyde 
• 673-32-5 1-Phenylprop-1-yne 
• 103-63-9 1-phenyl-2-bromoethane 
• 873-55-2 sodium benzenesulfonate 
• 27846-25-9 1-phenyl-2-(phenylsulfonyl)ethane 
• 64168-52-1 4'-nitrobenzenesulfenanilide 

Downstream Products

• 56836-93-2 3-methyl-4-phenylbutan-2-ol 
• 3968-86-3 2-methyl-1-phenylbutan-1-ol 
• 56253-64-6 (2-methyl-1-butenyl)-benzene 
• 40296-93-3 (Z,E)-2-methyl-1-phenylbut-2-ene 
• 772-46-3 2-methyl-1-phenyl-2-butanol 
• 106472-39-3 2-methyl-1-phenyl-2-hexanol 
• 74120-70-0 1-phenyl-2-methyl-2-octanol 
• 34126-21-1 3-methyl-4-phenyl-1-butanol 

Relevant academic research and scientific papers

Base-Mediated Radical Borylation of Alkyl Sulfones

A practical and direct method was developed for the production of versatile alkyl boronate esters via transition metal-free borylation of primary and secondary alkyl sulfones. The key to the success of the strategy is the use of bis(neopentyl glycolato) diboron (B2neop2), with a stoichiometric amount of base as a promoter. The practicality and industrial potential of this protocol are highlighted by its wide functional group tolerance, the late-stage modification of complex compounds, no need for further transesterification, and operational simplicity. Radical clock, radical trap experiments, and EPR studies were conducted which show that the borylation process involves radical intermediates.

Highly Efficient Enantioselective Synthesis of Chiral Sulfones by Rh-Catalyzed Asymmetric Hydrogenation

A highly efficient and enantioselective Rh-(R,R)-f-spiroPhos complex catalyzed hydrogenation of a series of unsaturated sulfones has been developed. With Rh-(R,R)-f-spiroPhos catalyst under mild conditions, not only the asymmetric hydrogenation of both the 3,3-diaryl and exocyclic α,β-unsaturated sulfones was first realized with up to 99.9% ee but also 3-alkyl-3-aryl and benzo[b]thiophene-1,1-dioxides were successfully hydrogenated to the corresponding chiral sulfones with excellent enantioselectivities (up to 99.4% ee) regardless of the steric hindrance, electronic property, and geometry of the substrates. Moreover, this reaction offers a route to (S)-(+)-ar-turmerone as a spice flavor, which is an important synthetic intermediate of pharmaceuticals.

Experimental and theoretical investigation of the enantiomerization of Lithium α-tert-butylsulfonyl carbanion salts and the determination of their structures in solution and in the crystal

Dynamic NMR (DNMR) spectroscopy of [R1C(R2)SO 2R3]Li (R1, R2 = alkyl, phenyl; R3 = Ph, tBu, adamantyl, CEt3) in [D8]THF has shown that the S-tBu, S-adamantyl, and S-CEt3 derivatives have a significantly higher enantiomerization barrier than their S-Ph analogues. C α-S bond rotation is most likely the rate-determining step of the enantiomerization of the salts bearing a bulky group at the S atom and two substituents at the Cα atom. Ab initio calculations on [Me(Ph)- SO 2tBu]- gave information about the two Cα-S rotational barriers, which are dominated by steric effects. Cryoscopy of [R1C(R 2)SO2tBu]Li in THF at -108°C revealed the existence of monomers and dimers. X-ray crystal structure analysis of the monomers and dimers of [R1C(R2)SO2tBu]Li·L n (R1 = Me, Et, tBuCH2, PhCH2, tBu; R2 = Ph, L = THF, 12-crown-4, PMDTA) and [R1C(R 2)SO2Ph]Li·2diglyme [R1 = R2 = Me, Et; R1-R2 = (CH2)5] showed them to be O-Li contact ion pairs (CIPs). The monomers and dimers have a Cα-S conformation in which the lone-pair orbital at the Cα atom bisects the O-S-O angle and a significantly shortened Cα-S bond. The Cα atom of [R1C(R2)SO2R 3]Li·Ln (R1 = Ph; R3 = Ph, tBu) is planar, whereas the Cα atom of [R1C(R 2)SO2R3]Li·Ln (R1 = R2 = alkyl) is strongly pyramidalized in the case of R3 = Ph and most likely planar for R3 = tBu. Ab initio calculations on [MeC- (Me)SO2R]- gave a pyramidalized Cα atom for R = Me and a nearly planar one for R = CF3 and tBu. The [R1C(R 2)SO2-tBu]Li salts were characterized by 1H, 13C, and 6Li NMR spectroscopy. 1H{ 1H} and 6Li{1H} NOE experiments are in accordance with the existence of O-Li CIPs. 1H and 13C NMR spectroscopy of [R1C(R2)SO2tBu]Li in [D 8]THF at low temperatures showed equilibrium mixtures of up to five different species being most likely monomeric and dimeric O-Li CIPs with different configurations. According to 7Li NMR spectroscopy, the addition of HMPA to [MeC(Ph)SO2tBu]Li in [D8]THF at low temperatures causes the formation of the separated ion pair [MeC(Ph)SO 2tBu]Li(HMPA)4.

Preparation of alcohols from sulfones and trialkylboranes

The reaction of sulfone anions with trialkylboranes followed by thermal isomerization of the obtained boron compounds in the presence of excess borane-methyl sulfide complex and by alkaline hydroperoxide oxidation yields primary alcohols.

Synthetic utility of 4'-nitrobenzenesulfenanilide in the functionalization of carbon-carbon double and triple bonds: Its use in the bromosulfenylation of alkenes and alkynes

The reaction of 4'-nitrobenzenesulfenanilide (NBSA) with hydrobromic acid, suitably carried out at room temperature in the presence of cyclohexene, trans-hex-3-ene, hex-1-ene and 3,3-dimethylbut-1-ene, results in quantitative isolation of corresponding 2-bromoalkyl phenyl sulfides which occur with trans-stereospecificity and anti-Markovnikov regiospecificity through electrophilic addition of initially-formed benzenesulfenyl bromide to the alkene double bond. Similar reaction in the presence of mono- and di- substituted alkyl- and phenyl-acetylenes generally affords (E)-2-bromovinyl phenyl sulfides in good yields, which become lower with decreasing nucleophilic power of the alkyne employed. However, in the presence of parent acetylene, no virtual formation of the corresponding sulfide adduct occurs, but almost exclusive formation of diphenyl disulfide essentially ascribable to preferred decomposition of the highly unstable benzenesulfenyl bromide intermediate. The present additions of benzenesulfenyl bromide to alkenes and alkynes are believed to involve the initial intermediacy of thiiranium- and thiirenium-like ions, respectively, by analogy with related Ad(E) reactions of sulfenyl chlorides.