Switchable Synthesis of Aryl Sulfones and Sulfoxides through Solvent-Promoted Oxidation of Sulfides with O<sub>2</sub>/Air
作者:Zhen Cheng、Pengchao Sun、Ailing Tang、Weiwei Jin、Chenjiang Liu
DOI:10.1021/acs.orglett.9b03192
日期:2019.11.15
A practical and switchable method for the synthesis of arylsulfones and sulfoxides via sulfide oxidation was developed. The chemoselectivities of products were simply controlled by reaction temperature using O2/air as the terminal oxidant and oxygen source. The broad substrate scope, easy realization of gram-scale production, and the simplification of a sulfide oxidation system render the strategy
Metal-Free Synthesis of Sulfones and Sulfoxides through Aldehyde-Promoted Aerobic Oxidation of Sulfides
作者:Lingyao Wang、Yuanbin Zhang、Jia Yao、Haoran Li
DOI:10.1007/s10562-021-03706-5
日期:2022.4
Metal-free aerobic oxidation of aryl sulfides to sulfoxides and sulfones has been developed in the presence of aliphatic aldehydes with excellent selectivity and yields. The reaction proceeded under mild conditions with the catalysis of N-hydroxyphthalimide (NHPI). Control experiments indicated that the reaction underwent a free radical pathway with the acylperoxyl radicals generated from aldehydes
A practical and efficient protocol for the switchable synthesis of sulfoxides, sulfones, and thiosulfonates via Selectfluor-mediated oxidation of sulfides and thiols, respectively, at ambient temperature has been developed. All these organosulfur compounds can be prepared with nearly quantitative yields by applying eco-friendly H2O as O-source. The formation of sulfoxides and thiosulfonates takes only
已经开发出一种实用且有效的方案,用于在环境温度下分别通过 Selectfluor 介导的硫化物和硫醇氧化合成亚砜、砜和硫代磺酸盐。所有这些有机硫化合物都可以通过使用环保的 H2O 作为 O 源以接近定量的收率制备。亚砜和硫代磺酸盐的形成仅需几分钟(3-20 分钟)。正如对照实验所表明的,氧化过程可能通过硫化物的氟化、与 的亲核加成和氟化氢的消除来进行。