Electrooxidation enables highly regioselective dearomative annulation of indole and benzofuran derivatives
| Autor: | Chunlan Song, Huiyue Yang, Wenxu Song, Kun Liu, Takfaoui Abdelilah, Yuqi Deng, Hengjiang Cong, Shan Tang, Shengchun Wang, Aiwen Lei |
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| Rok vydání: | 2020 |
| Předmět: |
Annulation
Science General Physics and Astronomy Synthetic chemistry methodology 010402 general chemistry 01 natural sciences Article General Biochemistry Genetics and Molecular Biology law.invention chemistry.chemical_compound law Electrochemistry Benzofuran lcsh:Science Electron paramagnetic resonance Indole test Multidisciplinary Catalytic mechanisms 010405 organic chemistry Regioselectivity General Chemistry Combinatorial chemistry 0104 chemical sciences chemistry Radical ion Yield (chemistry) lcsh:Q Cyclic voltammetry |
| Zdroj: | Nature Communications, Vol 11, Iss 1, Pp 1-11 (2020) Nature Communications |
| ISSN: | 2041-1723 |
| Popis: | The dearomatization of arenes represents a powerful synthetic methodology to provide three-dimensional chemicals of high added value. Here we report a general and practical protocol for regioselective dearomative annulation of indole and benzofuran derivatives in an electrochemical way. Under undivided electrolytic conditions, a series of highly functionalized five to eight-membered heterocycle-2,3-fused indolines and dihydrobenzofurans, which are typically unattainable under thermal conditions, can be successfully accessed in high yield with excellent regio- and stereo-selectivity. This transformation can also tolerate a wide range of functional groups and achieve good efficiency in large-scale synthesis under oxidant-free conditions. In addition, cyclic voltammetry, electron paramagnetic resonance (EPR) and kinetic studies indicate that the dehydrogenative dearomatization annulations arise from the anodic oxidation of indole into indole radical cation, and this process is the rate-determining step. Enriching the chemical space of polycyclic heterocycles is of high value in chemical biology. Here, the authors report an electrooxidative protocol for the regioselective dearomative annulation of indoles and benzofurans under undivided cell conditions and obtain five- to eight-membered fused heterocycles. |
| Databáze: | OpenAIRE |
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