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Atellura-Baeyer-Villiger oxidation: one-step transformation of tellurophene into chiral tellurinate lactone
Wang, Shitao; Yan, Chaoxian; Zhao, Wenlong; Liu, Xiaolan; Yuan, Cheng-Shan; Zhang, Hao-Li; Shao, Xiangfeng
2021-04-28
Source PublicationChemical Science
ISSN20416520
Volume12Issue:16Pages:5811-5817
AbstractBaeyer-Villiger (BV) oxidation is a fundamental organic reaction, whereas the hetero-BV oxidation is uncharted. Herein, atellura-BV oxidation is discovered. By oxidizing a tellurophene-embedded and electron-rich polycycle (1) withmCPBA or Oxone, an oxygen atom is inserted into the Te-C bond of the tellurophene to form tellurinate lactonemono-2. This reaction proceeds as follows: (i)1is oxidized to the tellurophene Te-oxide form (IM-1); (ii)IM-1undergoestellura-BV oxidation to givemono-2. Moreover, the hybrid trichalcogenasumanenes7and8are, respectively, converted to tellurinate lactonesmono-9andmono-10under the same conditions, indicating thattellura-BV oxidation shows high chemoselectivity. Due to the strong secondary bonding interactions between the TeO groups on tellurinate lactones,mono-2,mono-9, andmono-10are dimerized to form U-shaped polycycles2,9, and10, respectively. Notably,mono-2,mono-9,mono-10, and their dimers show chirality. This work enables one-step transformation of tellurophene into tellurinate lactone and construction of intricate polycycles. © The Royal Society of Chemistry 2021.
KeywordBaeyer Villiger oxidation Baeyer-Villiger Chemo-selectivity Electron-rich Organic reaction Oxygen atom Secondary bonding interactions Tellurophene Baeyer Villiger oxidation Baeyer-Villiger Chemo-selectivity Electron-rich Organic reaction Oxygen atom Secondary bonding interactions Tellurophene
PublisherRoyal Society of Chemistry
DOI10.1039/d1sc00397f
Indexed ByEI
Language英语
EI Accession Number20211910310083
EI KeywordsOxidation
EI Classification Number802.2 Chemical Reactions ; 804.1 Organic Compounds
Original Document TypeJournal article (JA)
Citation statistics
Cited Times:1[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.lzu.edu.cn/handle/262010/451298
Collection兰州大学
AffiliationState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou; 730000, China
First Author AffilicationCollege of Chemistry and Chemical Engineering
Recommended Citation
GB/T 7714
Wang, Shitao,Yan, Chaoxian,Zhao, Wenlong,et al. Atellura-Baeyer-Villiger oxidation: one-step transformation of tellurophene into chiral tellurinate lactone[J]. Chemical Science,2021,12(16):5811-5817.
APA Wang, Shitao.,Yan, Chaoxian.,Zhao, Wenlong.,Liu, Xiaolan.,Yuan, Cheng-Shan.,...&Shao, Xiangfeng.(2021).Atellura-Baeyer-Villiger oxidation: one-step transformation of tellurophene into chiral tellurinate lactone.Chemical Science,12(16),5811-5817.
MLA Wang, Shitao,et al."Atellura-Baeyer-Villiger oxidation: one-step transformation of tellurophene into chiral tellurinate lactone".Chemical Science 12.16(2021):5811-5817.
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