24422-78-4Relevant academic research and scientific papers
Cobalt-Catalyzed Redox-Neutral Sulfonylative Coupling from (Hetero)aryl Boronic Acids, Ammonium Salts and Potassium Metabisulfite
Zhang, Yingying,Zhu, Haibo,Fan, Qiangwen,Yang, Liu,Xie, Zongbo,Le, Zhang-Gao
, (2022/01/08)
An efficient cobalt-catalyzed redox-neutral sulfonylative coupling to afford (hetero)aryl alkyl sulfones from boronic acids, ammonium salts and potassium metabisulfite has been realized. Commercially available and air-stable CoCl2, in combination with phenanthroline ligand, is sufficient to achieve rapid and high-yielding conversion of the reactants into the corresponding sulfones. This practical transformation proceeds smoothly through C?N bond cleavage under redox-neutral catalytic conditions and shows broad functional-group tolerance. Other carbon based electrophiles, including diaryliodonium salts, heteroaryl halides, and carbonates were compatible. Further transformation of aryl alkyl sulfones then allows conversion into olefins, alkenyl sulfones and halogenated sulfones, respectively, in a one-pot process.
Method for alpha-position methylation of aryl benzyl sulfone compound
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Paragraph 0022-0044, (2020/11/23)
The invention discloses a method for alpha-position methylation of an aryl benzyl sulfone compound. The method comprises the following steps: sequentially adding the aryl benzyl sulfone compound, methanol, a metal precursor M, a ligand L, an alkaline substance and a solvent into a reactor, carrying out heating to 110-150 DEG C under the protection of nitrogen, conducting reacting for 20-30 hours,performing cooling to room temperature, conducting concentrating under reduced pressure, recovering the solvent and redundant methanol, and carrying out column chromatographic separation on residues to obtain the alpha-methylated aryl sulfone compound as shown in a formula (I). The method provided by the invention has the characteristics of easily available raw materials, simple operation, high chemical selectivity and regioselectivity and the like, meets the requirements of green chemistry, and has great implementation value and social and economic benefits.
Cu2O-catalyzed C–S coupling of quaternary ammonium salts and sodium alkane-/arene-sulfinates
Chen, Hongyi,Huang, Youming,Zeng, Qingle,Zheng, Wenting
, (2020/08/28)
A new protocol for the synthesis of (enantioenriched) benzylic sulfones via the Cu2O-catalyzed C–S bond cross coupling of alkane-/arene-sulfinates and (enantioenriched) benzylic quaternary ammonium salts has been developed. The product benzylic sulfones were obtained in good to high yields (75–96%). Chiral arylmethyl sulfones with high enantiomeric excess (90–94% ee) were also synthesized in the presence of Cu2O and 1,1′-bis-(diphenylphosphino)ferrocene (dppf).
Pyridine-catalyzed desulfonative borylation of benzyl sulfones
Maekawa, Yuuki,Ariki, Zachary T.,Nambo, Masakazu,Crudden, Cathleen M.
supporting information, p. 7300 - 7303 (2019/08/15)
Herein, we report the transition-metal free, pyridine-catalyzed desulfonative borylation of benzyl sulfones with bis(pinacolato)diboron (B2pin2). A variety of benzhydryl- and benzyl boronic esters could be synthesized from readily prepared sulfone derivatives. The borylation of cyclic sulfones accompanied by ring opening also proceeded to afford the corresponding sulfonate, which could be converted into functionalized sulfones and sulfonamides.
An efficient and straightforward route to terminal vinyl sulfones via palladium-catalyzed Suzuki reactions of α-bromo ethenylsulfones
Fang, Yewen,Yuan, Meijuan,Zhang, Juncong,Zhang, Li,Jin, Xiaoping,Li, Ruifeng,Li, Jinjian
, p. 1460 - 1463 (2016/03/12)
A general and simple protocol for the synthesis of α-substituted alkenylsulfones has been developed firstly via palladium-catalyzed Suzuki reactions between α-bromo ethenylsulfones and organoborons. Using a catalyst composed of Pd(OAc)2 and SPhos, a variety of aryl, heteroaryl, and alkylboron reagents could efficiently couple with α-bromo ethenylsulfones under mild conditions. Moreover, it has been demonstrated for the first time that vinyl sulfones underwent smooth reduction by diimide generated from 2-nitrobenzenesulfonylhydrazide.
Palladium-catalyzed Negishi α-arylation of alkylsulfones
Zhou, Gang,Ting, Pauline C.,Aslanian, Robert G.
experimental part, p. 939 - 941 (2010/05/18)
A general, mild catalytic system for α-monoarylation of various alkyl sulfones is described that utilizes palladium-catalyzed Negishi cross-coupling approach.
Highly selective 30% hydrogen peroxide oxidation of sulfides to sulfoxides using micromixing
Noguchi, Takuya,Hirai, Yoshiro,Kirihara, Masayuki
experimental part, p. 3040 - 3042 (2009/02/04)
The highly selective oxidation of sulfides to sulfoxides using 30% hydrogen peroxide has been achieved under catalyst-free conditions using a T-shaped micromixer. The Royal Society of Chemistry.
Dehydroxymethylation: an unusual reverse reaction of nucleophilic addition to formaldehyde
Peng, Lingling,Ma, Ming,Zhang, Xiu,Zhang, Shiwei,Wang, Jianbo
, p. 8175 - 8178 (2007/10/03)
An unusual dehydroxymethylation has been observed in an acyclic primary alcoholic system. The relief of steric congestion is considered as the primary driving force in this reaction.
Reaction of singlet oxygen with some benzylic sulfides
Bonesi, Sergio M.,Fagnoni, Maurizio,Monti, Sandra,Albini, Angelo
, p. 10716 - 10723 (2007/10/03)
Product distribution, total quenching rate (kT), and rate of chemical reaction (kr) with singlet oxygen have been determined for some alkyl, benzyl, α-methylbenzyl, and cumyl sulfides. Their contributions depend on the steric hindering around the sulfur atom. In protic solvents, the sulfoxide is the main product via a hydrogen-bonded persulfoxide. In apolar solvents, intramolecular α-H abstraction leads to oxidative C-S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines.
Reaction of α-benzenesulfonylphenylacetic acid with alkyl halides. Decarboxylative alkylation vs. decarboxylative protonation
Wladislaw, Blanka,Perna, Fernando,De Almeida Neves, Regina Maria,Marzorati, Liliana,Di Vitta, Claudio
, p. 1403 - 1409 (2007/10/03)
The reaction of α-benzenesulfonylphenylacetic acid with some alkyl halides, using as base NaH in DMSO, leads to decarboxylative protonation to give benzylphenylsulfone. Decarboxylative alkylation occurs only when CO2 is expelled by flushing with nitrogen. The mechanism of the decarboxylative protonation is investigated.
