兰州大学机构库 >化学化工学院
A tellura-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
2021-03
Source PublicationCHEMICAL SCIENCE
ISSN2041-6520
AbstractBaeyer-Villiger (BV) oxidation is a fundamental organic reaction, whereas the hetero-BV oxidation is uncharted. Herein, a tellura-BV oxidation is discovered. By oxidizing a tellurophene-embedded and electron-rich polycycle (1) with mCPBA or Oxone, an oxygen atom is inserted into the Te-C bond of the tellurophene to form tellurinate lactone mono-2. This reaction proceeds as follows: (i) 1 is oxidized to the tellurophene Te-oxide form (IM-1);(ii) IM-1 undergoes tellura-BV oxidation to give mono-2. Moreover, the hybrid trichalcogenasumanenes 7 and 8 are, respectively, converted to tellurinate lactones mono-9 and mono-10 under the same conditions, indicating that tellura-BV oxidation shows high chemoselectivity. Due to the strong secondary bonding interactions between the Te=O groups on tellurinate lactones, mono-2, mono-9, and mono-10 are dimerized to form U-shaped polycycles 2, 9, and 10, 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.
PublisherROYAL SOC CHEMISTRY
DOI10.1039/d1sc00397f
Indexed ByEI ; SCOPUS ; SCIE
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000631720200001
Citation statistics
Cited Times:1[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.lzu.edu.cn/handle/262010/449393
Collection化学化工学院
Corresponding AuthorShao, Xiangfeng
AffiliationLanzhou Univ, State Key Lab Appl Organ Chem, Tianshui Southern Rd 222, Lanzhou 730000, Peoples R China
First Author AffilicationCollege of Chemistry and Chemical Engineering
Corresponding Author AffilicationCollege of Chemistry and Chemical Engineering
Recommended Citation
GB/T 7714
Wang, Shitao,Yan, Chaoxian,Zhao, Wenlong,et al. A tellura-Baeyer-Villiger oxidation: one-step transformation of tellurophene into chiral tellurinate lactone[J]. CHEMICAL SCIENCE,2021.
APA Wang, Shitao.,Yan, Chaoxian.,Zhao, Wenlong.,Liu, Xiaolan.,Yuan, Cheng-Shan.,...&Shao, Xiangfeng.(2021).A tellura-Baeyer-Villiger oxidation: one-step transformation of tellurophene into chiral tellurinate lactone.CHEMICAL SCIENCE.
MLA Wang, Shitao,et al."A tellura-Baeyer-Villiger oxidation: one-step transformation of tellurophene into chiral tellurinate lactone".CHEMICAL SCIENCE (2021).
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