A tellura-Baeyer–Villiger oxidation: one-step transformation of tellurophene into chiral tellurinate lactone. Issue 16 (22nd March 2021)

• Record Type: Journal Article
• Authors: Wang, Shitao; Yan, Chaoxian; Zhao, Wenlong; Liu, Xiaolan; Yuan, Cheng-Shan; Zhang, Hao-Li; Shao, Xiangfeng
• Is Part Of: Chemical science. Volume 12:Issue 16(2021)
• Page Start: 5811
• Page End: 5817
• Publication Date: 2021-03-22
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc00397f
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : 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. Abstract : 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 m CPBA 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.