Iridium‐Catalyzed Intermolecular Dehydrogenative Silylation of Polycyclic Aromatic Compounds without Directing Groups |
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Authors: | Dr. Masahito Murai Keishi Takami Prof. Dr. Kazuhiko Takai |
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Affiliation: | Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, 3‐1‐1, Tsushimanaka, Kita‐ku, Okayama 700‐8530 (Japan), Fax: (+81)?86‐251‐8094 |
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Abstract: | This study describes the iridium‐catalyzed intermolecular dehydrogenative silylation of C(sp2)?H bonds of polycyclic aromatic compounds without directing groups. The reaction produced various arylsilanes through both Si?H and C?H bond activation, with hydrogen as the sole byproduct. Reactivity was affected by the electronic nature of the aromatic compounds, and silylation of electron‐deficient and polycyclic aromatic compounds proceeded efficiently. Site‐selectivity was controlled predominantly by steric factors. Therefore, the current functionalization proceeded with opposite chemo‐ and site‐selectivity compared to that observed for general electrophilic functionalization of aromatic compounds. |
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Keywords: | C H bond activation dehydrogenation iridium polycyclic aromatic compounds silylation |
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