3079-28-5Relevant articles and documents
Highly Selective Direct Oxidation of Thioethers to Sulfoxides Using Molecular Oxygen
Correa, Paul E.,Riley, Dennis P.
, p. 1787 - 1788 (1985)
Dialkyl sulfides are converted to sulfoxides in high yield by use of molecular oxygen, ca. 40-atm pressure, and polar solvents.
The Novel Cerium(IV)-catalysed Molecular Oxygen Oxidation of Thioethers to Sulphoxides
Riley, Dennis P.,Correa, Paul E.
, p. 1097 - 1098 (1986)
Thioethers can be oxidized with catalytic amounts of Ce(IV) salts rapidly and selectively to sulphoxides using molecular oxygen (PO2 = 5-15 bar) as the oxidant.
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.
Selective Synthesis of Sulfoxides through Oxidation of Sulfides with Sodium Hypochlorite Pentahydrate Crystals
Okada, Tomohide,Matsumuro, Hiroaki,Kitagawa, Saori,Iwai, Toshiaki,Yamazaki, Kento,Kinoshita, Yukari,Kimura, Yoshikazu,Kirihara, Masayuki
, p. 2547 - 2552 (2015/11/16)
Oxidation of sulfides with sodium hypochlorite pentahydrate crystals (1.1 equiv) in an aqueous acetonitrile solution selectively produces the corresponding sulfoxides in high yields. This procedure is catalyst-free and environmentally benign.
Alloxazine-cyclodextrin conjugates for organocatalytic enantioselective sulfoxidations
Mojr, Viktor,Budesinsky, Milos,Cibulka, Radek,Kraus, Tomas
experimental part, p. 7318 - 7326 (2011/12/03)
Four structurally different alloxazine-cyclodextrin conjugates were prepared and tested as catalysts for the enantioselective oxidation of prochiral sulfides to sulfoxides by hydrogen peroxide in aqueous solutions. The alloxazinium unit was appended to the primary face of α- and β-cyclodextrins via a linker with variable length. A series of sulfides was used as substrates: n-alkyl methyl sulfides (n-alkyl = hexyl, octyl, decyl, dodecyl), cyclohexyl methyl sulfide, tert-butyl methyl sulfide, benzyl methyl sulfide and thioanisol. α-Cyclodextrin conjugate having alloxazinium unit attached via a short linker proved to be a suitable catalyst for oxidations of n-alkyl methyl sulfides, displaying conversions up to 98% and enantioselectivities up to 77% ee. β-Cyclodextrin conjugates were optimal catalysts for the oxidation of sulfides carrying bulkier substituents; e.g. tert-butyl methyl sulfide was oxidized with quantitative conversion and 91% ee. Low loadings (0.3-5 mol%) of the catalysts were used. No overoxidation to sulfones was observed in this study.
