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Issue 12, 2017
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Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides

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Abstract

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.

Graphical abstract: Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides

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Publication details

The article was received on 05 Jan 2017, accepted on 26 Feb 2017 and first published on 28 Feb 2017


Article type: Paper
DOI: 10.1039/C7OB00021A
Citation: Org. Biomol. Chem., 2017,15, 2647-2654
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    Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides

    S. Gan, J. Yin, Y. Yao, Y. Liu, D. Chang, D. Zhu and L. Shi, Org. Biomol. Chem., 2017, 15, 2647
    DOI: 10.1039/C7OB00021A

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