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Gan S, Yin J, Yao Y, et al. Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides. Org Biomol Chem. 2017;15(12):2647-2654doi: 10.1039/c7ob00021a.
Gan, S., Yin, J., Yao, Y., Liu, Y., Chang, D., Zhu, D., & Shi, L. (2017). Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides. Organic & biomolecular chemistry, 15(12), 2647-2654. https://doi.org/10.1039/c7ob00021a
Gan, Shaoyan, et al. "Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides." Organic & biomolecular chemistry vol. 15,12 (2017): 2647-2654. doi: https://doi.org/10.1039/c7ob00021a
Gan S, Yin J, Yao Y, Liu Y, Chang D, Zhu D, Shi L. Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides. Org Biomol Chem. 2017 Mar 22;15(12):2647-2654. doi: 10.1039/c7ob00021a. PMID: 28267186.
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Org Biomol Chem. 2017 Mar 22;15(12):2647-2654. doi: 10.1039/c7ob00021a.

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

Organic & biomolecular chemistry

Shaoyan Gan, Junjie Yin, Yuan Yao, Yang Liu, Denghu Chang, Dan Zhu, Lei Shi

Affiliations

  1. MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China. [email protected] and Shenzhen Graduate School, Harbin Institute of Technology, Shenzhen 518055, China.
  2. MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China. [email protected].
  3. MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China. [email protected] and Shenzhen Graduate School, Harbin Institute of Technology, Shenzhen 518055, China and State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.

PMID: 28267186 DOI: 10.1039/c7ob00021a

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.

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