134235-93-1Relevant articles and documents
Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides
Gan, Shaoyan,Yin, Junjie,Yao, Yuan,Liu, Yang,Chang, Denghu,Zhu, Dan,Shi, Lei
supporting information, p. 2647 - 2654 (2017/04/03)
Metal- and additive-free oxidation of a series of sulfides/thioketones has been achieved using cyclic diacyl peroxides as mild oxygen sources. This protocol features simple manipulation, high chemo- and diastereoselectivity, and a broad substrate scope (up to 42 examples), tolerates many common functional groups, and is scalable and applicable to the late-stage sulfoxidation strategy. A preliminary mechanistic study by quantum mechanical calculations suggests that a single two-electron transfer process is energetically more favorable, and indicates the reactivity of cyclic diacyl peroxides distinct from conventional acyclic acyl peroxides.
Chiral phosphoric acid-catalyzed asymmetric oxidation of aryl alkyl sulfides and aldehyde-derived 1,3-dithianes: Using aqueous hydrogen peroxide as the terminal oxidant
Liu, Zhao-Min,Zhao, Hua,Li, Mei-Qiu,Lan, Yu-Bao,Yao, Qi-Bo,Tao, Jing-Chao,Wang, Xing-Wang
supporting information; experimental part, p. 1012 - 1022 (2012/05/20)
(R)-1,1'-Binaphthyl-2,2'-diol (R-BINOL) derived chiral phosphoric acids have been explored as organocatalysts for the asymmetric oxidation of a series of aryl alkyl sulfides and 1,3-dithianes derived from aldehydes with aqueous hydrogen peroxide (H2O2) as the terminal oxidant. The enantiomerically enriched sulfoxides are obtained in moderate to excellent yield (up to 99%) with excellent diastereoselectivity (up to >99:1 dr) and moderate to good enantioselectivity (up to 91:9 er). In particular, the present protocol stereoselectively provides an efficient access to enantiomerically enriched aryl alkyl sulfoxides and dithioacetal mono-sulfoxides, which strictly restrains the formation of the undesirable by-products: sulfones or disulfoxides. The tracking experiments also verify that this approach proceeds via a direct sulfoxidation process, instead of a kinetic resolution route by overoxidation of the resulting sulfoxides. Copyright
An efficient solvent free catalytic oxidation of sulfides to sulfoxides with hydrogen peroxide catalyzed by a binaphthyl-bridged Schiff base titanium complex
De Rosa, Margherita,Lamberti, Marina,Pellecchia, Claudio,Scettri, Arrigo,Villano, Rosaria,Soriente, Annunziata
, p. 7233 - 7235 (2007/10/03)
A titanium binaphthyl-bridged Schiff base complex proved to be an efficient catalyst for the hydrogen peroxide oxidation of aromatic and aliphatic sulfides to the corresponding sulfoxides in satisfactory yields under solvent-free conditions.
