3406-03-9Relevant articles and documents
Controlled Synthesis of β-Keto Sulfones and Vinyl Sulfones under Electrochemical Oxidation
Fang, Yang,Xu, Dongping,Yu, Yingliang,Tang, Rumeng,Dai, Shuaishuai,Wang, Zhenghua,Zhang, Wu
, (2022/04/09)
Selective sulfonylation and oxosulfonylation of alkenes with sulfinates have been developed via anodic oxidation in an undivided cell. The novel electrosynthetic method provided β-keto sulfones and vinyl sulfones with good to excellent yields in the absence of any transition metal catalyst and oxidants. Mechanism studies show that two different pathways involved in these two transformations.
Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals
Das, Sanju,De Sarkar, Suman,Mandal, Tanumoy
, (2021/12/10)
A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.
A glucose oxidase-hemoglobin system for efficient oxysulfonylation of alkenes/alkynes in water
Li, Chen,Li, Fengxi,Li, Zhengqiang,Liu, Jiaxu,Su, Jiali,Wang, Chunyu,Wang, Lei,Xu, Yaning,Yu, Yue
, (2020/12/29)
Background: β-ketosulfones are important bioactive compounds that have been extensively studied in organic chemistry. In this work, a green and efficient process for the synthesis of β-ketosulfones from alkenes (1) or alkynes (3) with sodium benzenesulfinate (2) was developed. Results: Under optimal conditions (alkenes (0.5 mmol) or alkynes (0.5 mmol), sodium benzenesulfinate (0.5 mmol), water (2 mL), hemoproteins (heme concentration: 0.06 mol%), GOX (42 U/ml), room temperature, 2 h), high yields of β-ketosulfones could be obtained when HgbRb (hemoglobin from rabbit blood) and GOX (glucose oxidase from Aspergillus niger) was used as the catalyst. Conclusion: This enzymatic method demonstrates the great potential for the synthesis of β-ketosulfones and extends the application of dual protein systems in organic synthesis.
