Abstract
A mild and practical protocol for selectively time-dependent dehydrogenative C-C coupling, as well as tandem coupling-cyclization reaction between indoles or/and other heteroaromatics via electrochemically oxidative process has been demonstrated. The reaction runs under noble catalyst, external oxidant and inert gas free condition, allowing tunable access to a wide variety of synthetically useful symmetrical or nonsymmetrical heteroarene with aggregation-induced emission (AIE), and polycyclic 3-D indole derivatives with aggregation-caused quenching (ACQ) fluorescence properties. Finally, preliminary mechanistic study indicated that tunable generation of indole cation under various electrolysis potential via regulating N-protecting group was the key to achieve cross-coupling between indoles and other heteroaromatics.
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Acknowledgements
This work was supported by Guangdong Basic and Applied Basic Research Foundation (2019A1515011743), the Pearl River talent program of Guangdong Province (Youth Top-Notch Talent, 2017GC010302), and Jinan University. We thank Dr. Xiaodan Chen for useful discussions and advice during preparation of the manuscript
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Electrochemically time-dependent oxidative coupling/coupling-cyclization reaction between heterocycles: tunable synthesis of polycyclic indole derivatives with fluorescence properties
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Ning, Z., Zhang, Z., Yan, Q. et al. Electrochemically time-dependent oxidative coupling/coupling-cyclization reaction between heterocycles: tunable synthesis of polycyclic indole derivatives with fluorescence properties. Sci. China Chem. 65, 1962–1967 (2022). https://doi.org/10.1007/s11426-022-1289-9
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DOI: https://doi.org/10.1007/s11426-022-1289-9