Regioselective Electrochemical Hydroalkylations of [60]Fullerene-Fused Furochromenone
Zheng-Chun Yin
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorChuang Niu
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorMingjie Li
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorWen-Rui Liu
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorCorresponding Author
Guan-Wu Wang
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, 730000 China
E-mail: [email protected]Search for more papers by this authorZheng-Chun Yin
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorChuang Niu
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorMingjie Li
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorWen-Rui Liu
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorCorresponding Author
Guan-Wu Wang
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, 730000 China
E-mail: [email protected]Search for more papers by this author† Dedicated to the Special Issue of Recent Advances in Fullerene Chemistry.
Comprehensive Summary
Regioselective electrochemical hydroalkylations of [60]fullerene-fused furochromenone with alky halides under different acidic conditions unexpectedly afford three types of tetra-functionalized [60]fullerene derivatives in high yields. When acetic acid is used as the proton source, two 1,2,3,4-adducts with retained or rearranged five-membered heterocycle are obtained as major and minor products, respectively. While trifluoroacetic acid is employed as the proton source, 1,2,3,16-adducts and 1,2,3,4-adducts, both with the five-membered heterocycle rearranged from [6,6]-junction to [5,6]-junction, are generated. Intriguingly, the obtained 1,2,3,16-adducts can be transformed into 1,2,3,4-adducts accompanied by rearrangement of the fused five-membered heterocycle from [5,6]-junction to [6,6]-junction. These products have been characterized by spectroscopic data and single-crystal X-ray analysis. Moreover, the two 1,2,3,4-adducts with the heterocycle fused to [5,6]-junction or [6,6]-junction show diagnostic UV-vis spectra, which may be useful for the identification of these two types of 1,2,3,4-adducts in the future. A plausible reaction mechanism has been proposed to elucidate the formation of hydroalkylation products in the presence of different acids.
Supporting Information
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Appendix S1: Supporting Information |
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