A tellura-Baeyer–Villiger oxidation: one-step transformation of tellurophene into chiral tellurinate lactone†‡
| Autor: | Chengshan Yuan, Wenlong Zhao, Xiaolan Liu, Chaoxian Yan, Shitao Wang, Hao-Li Zhang, Xiangfeng Shao |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | Chemical Science |
| ISSN: | 2041-6539 2041-6520 |
| Popis: | Baeyer–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 Created by potrace 1.16, written by Peter Selinger 2001-2019 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. A tellura-Baeyer–Villiger oxidation is discovered, which enables one-step transformation of tellurophene into chiral tellurinate lactones. The resulting tellurinate lactones are dimerized in the solid state to form U-shaped polycycles. |
| Databáze: | OpenAIRE |
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