Reductive Hydrogenation of Cs-C70(CF3)8 and C1-C70(CF3)10

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• 作者：Victor A. Brotsman ; Viktor P. Bogdanov ; Alexey V. Rybalchenko ; Evgenia P. Galanicheva ; Nikita M. Belov ; Dr. Vitaliy Yu. Markov ; Dr. Natalia S. Lukonina ; Dr. Ilya N. Ioffe ; Prof. Dr. Sergey I. Troyanov ; Prof. Dr. Erhard Kemnitz and Dr. Alexey A. Goryunkov
• 刊名：Chemistry – An Asian Journal
• 出版年：2016
• 出版时间：July 5, 2016
• 年：2016
• 卷：11
• 期：13
• 页码：1945-1954
• 全文大小：1901K
• ISSN：1861-471X

文摘

CF₃-derivatized fullerenes prove once again to be promising scaffolds for regioselective fullerene functionalization: now with the smallest possible addends—hydrogen atoms. Hydrogenation of C_s-C₇₀(CF₃)₈ and C₁-C₇₀(CF₃)₁₀ by means of reduction with Zn/Cu couple in the presence of water proceeds regioselectively, yielding only one major isomer of C₇₀(CF₃)₈H₂ and only two for C₇₀(CF₃)₁₀H₂, whose addition patterns are combined in the only abundant isomer of C₇₀(CF₃)₁₀H₄. The observed selectivity is governed by the electronic structure of trifluoromethylated substrates. Interestingly, we discovered that Clar's theory can be utilized to predict the regiochemistry of functionalization, and we look forward to testing it on forthcoming cases of derivatization of pre-functionalized fullerene building blocks.