28658-34-6

Upstream product

• 4547-64-2 4-methoxybenzenesulfonyl azide 
• 24850-33-7 allyltributylstanane 
• 76-63-1 allytriphenyltin 
• 6462-50-6 sodium 4-methoxybenzenesulfinate 
• 106-95-6 allyl bromide 
• 2550-04-1 allyltriethoxysilane 
• 696-62-8 para-iodoanisole 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 5720-07-0 4-methoxyphenylboronic acid 
• 21130-91-6 triethoxy(4-methoxyphenyl)silane 
• 2551-83-9 allyltrimethoxysilane 
• 107-05-1 3-chloroprop-1-ene 
• 37780-82-8 4-methoxyphenyl allyl sulfide 
• 1709-60-0 4-methoxybenzenesulfinic acid 

Downstream Products

• 1260118-83-9 1-(4-(3-((4-methoxyphenyl)sulfonyl)propyl)phenyl)ethanone 
• 3112-80-9 bis(p-anisyl)sulfone 
• 1216-95-1 p-tolyl p-methoxyphenyl sulfone 
• 28691-73-8 1-Propenyl--sulfon 

Relevant academic research and scientific papers

A General Photocatalytic Route to Prenylation

Prenylation is an essential reaction on which nature relies to modify properties of molecules and build terpenoids, but remains a challenging chemical reaction. Aiming to capitalize on recent advances in photocatalysis to easily and cleanly generate a broad range of carbon based radicals, we have developed a prenyl transfer reagent that is captured by transiently generated radicals. The reagent can be made in bulk, is bench stable, and broadly applicable such that it can be used with existing photocatalytic methods with very few changes to reaction conditions. Ultimately, this provides a true drop-in solution for prenylation, expanding the scope of substrates that can be readily prenylated.

SO2 conversion to sulfones: Development and mechanistic insights of a sulfonylative Hiyama cross-coupling

A Pd-catalyzed Hiyama cross-coupling reaction using SO2 is described. The use of silicon-based nucleophiles leads to the formation of allyl sulfones under mild conditions with a broad functional group tolerance. Control experiments coupled with DFT calculations shed light on the key steps of the reaction mechanism, revealing the crucial role of a transient sulfinate anion.

Acenaphthoimidazolylidene Gold Complex-Catalyzed Alkylsulfonylation of Boronic Acids by Potassium Metabisulfite and Alkyl Halides: A Direct and Robust Protocol to Access Sulfones

A robust acenaphthoimidazolylidene gold complex is demonstrated as a highly efficient catalyst in the direct alkylsulfonylation of boronic acids. Remarkably, a wide range of highly reactive and unreactive C-electrophiles were well-tolerated to produce various (hetero)aryl-alkyl, aryl-alkenyl, and alkenyl-alkyl sulfones in satisfactory yields with 5 mol % catalyst loading. Along with the steric properties of NHC ligands, the high catalytic activity of this gold complex suggests that the strong σ-donation of acenaphthoimidazolylidene also played a role in promoting this challenging redox-neutral catalytic process.

Process for the Synthesis of Sulfones and Sulfonamides

A one pot single step process is described for the synthesis of a compound, including a labeled compound, containing a sulfonyl functional group comprising the step of mixing together a silane, an SO2 source, an electrophilic compound, an activ

Efficient synthesis of aliphatic sulfones by Mg mediated coupling reactions of sulfonyl chlorides and aliphatic halides

Sulfonyl chlorides were reduced to anhydrous sulfinate salts with magnesium under sonication. These sulfinates were alkylated to sulfones with alkyl chlorides in the presence of catalytic sodium iodide under sonication. A variety of aliphatic sulfones was efficiently prepared by this one-pot two-step procedure.

Metal and solvent free selective oxidation of sulfides to sulfone using bifunctional ionic liquid [pmim]IO4

The oxidation of organo-sulfides to sulfones has been accomplished using an easily accessible bifunctional ionic liquid, [pmim]IO4 in the absence of any other oxidants, metal and organic solvent at ambient temperature. A variety of sulfides including dialkyl, aryl-alkyl, diaryl, and aryl-hetero aryl have been oxidized to the corresponding functionalized sulfones in high yields by this procedure.

Hydride affinities of cumulated, isolated, and conjugated dienes in acetonitrile

(Chemical Equation Presented) The hydride affinities (defined as the enthalpy changes in this work) of 15 polarized dienes [five phenyl sulfone substituted allenes (1a), the corresponding five isolated dienes (1b), and the corresponding five conjugated dienes (1c)] in acetonitrile solution were determined by titration calorimetry for the first time. The results display that the hydride affinity scales of the 15 dienes in acetonitrile range from -71.6 to -73.9 kcal/mol for 1a, from -46.2 to -49.7 kcal/mol for 1b, and from -45.0 to -46.5 kcal/mol for 1c, which indicates that the hydride-obtaining abilities of the cumulated dienes (1a) are not only much larger than those of the corresponding conjugated dienes (1c) but also much larger than those of the corresponding isolated dienes (1b). The hydrogen affinities of the 15 dienes as well as the hydrogen affinities and the proton affinities of the radical anions of the dienes (1-.) in acetonitrile were also evaluated by using relative thermodynamic cycles according to Hess's law. The results show that (i) the hydrogen affinities of the neutral dienes 1 cover a range from -44.5 to -45.6 kcal/mol for 1a, from -20.4 to -21.4 kcal/ mol for 1b, and from -17.3 to -18.5 kcal/mol for 1c; (ii) the hydrogen affinities of the radical anions of the dienes (1-.) in acetonitrile cover a range from -40.6 to -47.2 kcal/mol for 1a-., from -21.6 to -29.6 kcal/mol for 1b-., and from -10.0 to -15.4 kcal/mol for 1c-.; (iii) the proton affinities of the 15 1a-. in acetonitrile cover a range from -97.0 to -100.6 kcal/mol for 1a-., from -77.8 to -83.4 kcal/ mol for 1b -., and from -66.2 to -68.9 kcal/mol for 1c-.. The main reasons for the great difference between the cumulated dienes and the corresponding isolated and conjugated dienes in the hydride affinity, hydrogen affinity, and proton affinity have been examined. It is evident that these experimental results should be quite valuable to facilitate the elucidation of the origins of the especially high chemical potencies of the allenes, the choice of suitable hydride reducing agents to reduce the dienes, and the analyses on the reduction mechanisms.

Radical-chain reactions of sulfonyl azides and of ethyl azidoformate with allylstannanes: Homolytic allylation at nitrogen

4-Methylbenzenesulfonyl azide reacts with allyltriphenylstannane (ATPS) in refluxing benzene, in the presence of 2,2′-azobis(2-methylpropionitrile) as initiator, to give N-allyl-4-methylbenzenesulfonamide in good yield after hydrolytic work-up. Small amounts of allyl 4-methylphenyl sulfone were also formed. The reaction follows a free-radical chain mechanism which involves competitive addition of Ph5Sn? to Na and to Nc of the azido group in ArSO2NaNbNc. Addition to Na followed by loss of nitrogen gives ArSO2NSnPh3, the precursor of the N-allylarenesulfonamide, while addition to Nc leads to the formation of ArSO2 and thence to the allyl aryl sulfone. Allyltrimethylstannane behaves in a similar way to ATPS, but allyltributylstannane gives only a low yield of N-allylarenesulfonamide and the major product is the unsubstituted sulfonamide MeC6H4SO2NH2, which results because the radical ArSO2NSnBu3 undergoes intramolecular 1,5-hydrogen-atom transfer in preference to adding to the allylstannane. 2-Methylallyltriphenylstannane reacts in an analogous way to ATPS, but allylstannanes containing non-terminal double bonds do not react successfully. The arenesulfonyl azides 4-XC6H4SO2N3 (X = H, MeO, F) react in a similar way to tosyl azide, but the reaction is very sluggish when X = NO2? With 1-octanesulfonyl azide, reaction with Ph3Sn? is much less selective and products arising from attack at Na and Nc are formed in comparable yields. Ethyl azidoformate reacts with allylstannanes in a similar manner to, although more slowly than, tosyl azide and gives good yields of the corresponding allylic carbamates.

Thermal Decomposition of some Allyl Methoxyarenesulphinates

The thermal decomposition of some allyl methoxyarenesulphinates in boiling acetic acid has been studied.The principal products are the diaryl sulphides together with small amounts of the aryl arenethiosulphonates, diaryl sulphoxides, diaryl sulphones, aromatic hydrocarbons, and in one case, some of the allyl aryl sulphone.

THERMAL AND PHOTOCHEMICAL REACTIONS OF ALLYLCOBALOXIMES WITH para-SUBSTITUTED BENZENESULPHONYL CHLORIDE UNDER AEROBIC AND ANAEROBIC CONDITIONS

The compounds p-XC6H4SO2Cl (X = Cl, Br, I, OMe) react regiospecifically with allyl-, 2-methylallyl-, 3-methylallyl- and 3,3-dimethyl-cobaloximes under thermal and photochemical conditions.A rearranged organic product is obtained in each case.The yields are much better in photochemical reactions.A chain mechanism is involved in which the organosulphonyl radical and cobaloxime(II) are the chain propagating species.Yields of the sulphones are drastically reduced when the reactions are carried out in the presence of oxygen.