Palladium‐Catalyzed CH Fluorosilylation of 2‐Phenylpyridines: Synthesis of Silafluorene Equivalents |
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| Authors: | Dr. Qing Xiao Dr. Xiangtai Meng Prof. Dr. Motomu Kanai Prof. Dr. Yoichiro Kuninobu |
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| Affiliation: | Graduate School of Pharmaceutical Sciences, The University of Tokyo, ERATO (Japan) Science and Technology Agency (JST), Kanai Life Science Catalysis Project, 7‐3‐1 Hongo, Bunkyo‐ku, Tokyo 113‐0033 (Japan) |
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| Abstract: | Treatment of 2‐phenylpyridines with amino(1,3,2‐dioxaborolan‐2‐yl)diphenylsilane produced fluorosilylated 2‐phenylpyridines in good to excellent yields under palladium catalysis. This reaction is the first example of C? H fluorosilylation. Single‐crystal X‐ray structure analysis revealed a Lewis acid–base interaction between the silicon and nitrogen atoms, and the obtained fluorosilylated products are silafluorene equivalents. The fluorosilylated products showed stronger fluorescence than the corresponding silafluorene derivative. |
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| Keywords: | C H activation fluorescence heterocycles palladium silicon |
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