1260149-71-0Relevant academic research and scientific papers
Dioxygen-triggered oxidative radical reaction: Direct aerobic difunctionalization of terminal alkynes toward β-keto sulfones
Lu, Qingquan,Zhang, Jian,Zhao, Ganglu,Qi, Yue,Wang, Huamin,Lei, Aiwen
, p. 11481 - 11484 (2013)
An unprecedented dioxygen-triggered oxidative radical process was explored using dioxygen as the solely terminal oxidant, realizing aerobic oxidaitve difunctionalization of terminal alkynes toward β-keto sulfones with high selectivity. Operando IR experiments revealed that pyridine not only acts as a base to successfully surpress ATRA (atom transfer radical addition) process, but also plays a vital role in reducing the activity of sulfinic acids.
Manganese(III)-Mediated and -Catalyzed Decarboxylative Hydroxysulfonylation of Arylpropiolic Acids with Sodium Sulfinates in Water
Xiong, Yan-Shi,Weng, Jiang,Lu, Gui
supporting information, p. 1611 - 1616 (2018/03/05)
With water as both solvent and reactant, a novel manganese(III)-mediated and -catalyzed synthesis of β-ketosulfones through decarboxylative hydroxysulfonylation reactions of arylpropiolic acids with sodium sulfinates is described. This protocol has the advantages of mild reaction conditions, short reaction time, easy to handle reagents, purification simplicity, and being environmentally benign, which demonstrate the practical utility of this methodology. (Figure presented.).
Aerobic oxidation in nanomicelles of aryl alkynes, in water at room temperature
Handa, Sachin,Fennewald, James C.,Lipshutz, Bruce H.
, p. 3432 - 3435 (2014/04/03)
On the basis of the far higher solubility of oxygen gas inside the hydrocarbon core of nanomicelles, metal and peroxide free aerobic oxidation of aryl alkynes to β-ketosulfones has been achieved in water at room temperature. Many examples are offered that illustrate broad functional group tolerance. The overall process is environmentally friendly, documented by the associated low E Factors. It's all happenin' in the micelle! The highly preferential dissolution of oxygen gas within the lipophilic cores inside nanomicelles leads to efficient trapping of in situ generated vinyl radicals. These intermediate radicals, derived from arylalkynes and sulfinic acids, lead to β-ketosulfone products, formed under especially mild and green conditions: no metals, no heating or cooling, recyclable aqueous media, and low E Factors.
Rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/ arylsulfonyl)acetonitriles: Efficient synthesis of (Z)-β- sulfonylvinylamines and β-Keto sulfones
Tsui, Gavin Chit,Glenadel, Quentin,Lau, Chan,Lautens, Mark
supporting information; experimental part, p. 208 - 211 (2011/03/19)
An efficient rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitrile is described. Novel β-sulfonylvinylamine products are formed in a stereoselective fashion (Z-alkene). Upon hydrolysis, useful β-keto sulfones are obtained with a broad scope of aryl and sulfonyl substituents.
