Naka Akinobu, Shimomura Natsumi, Kobayashi Hisayoshi
Department of Life Science, Kurashiki University of Science and the Arts, 2640 Nishinoura, Tsurajima, Kurashiki, Okayama 712-8505, Japan.
Professor Emeritus, Kyoto Institute of Technology, Matsugasaki, Kyoto 606-8585, Japan.
ACS Omega. 2022 Aug 16;7(34):30369-30375. doi: 10.1021/acsomega.2c03637. eCollection 2022 Aug 30.
Silole derivatives are attracting significant attention as new functional materials with excellent electronic and photophysical properties. Thus, the development of synthesis methods to afford such derivatives is highly desirable. Herein, the synthesis of pyridine-fused siloles under the conditions of the Sonogashira coupling reaction is described. The reactions of 2-bromo-3-(pentamethyldisilanyl)pyridine () with ethynylbenzene derivatives in the presence of PdCl(PPh)-CuI as a catalyst afforded the corresponding pyridine-fused siloles (-) through intramolecular -bis-silylation. DFT calculations were also performed to understand the reaction mechanism. This paper is the first to report on the successful use of palladium catalysts in the -bis-silylation of alkynes with disilanes.
硅杂环戊二烯衍生物作为具有优异电子和光物理性质的新型功能材料正引起广泛关注。因此，开发能够合成此类衍生物的方法非常必要。本文描述了在Sonogashira偶联反应条件下吡啶稠合硅杂环戊二烯的合成。2-溴-3-(五甲基二硅烷基)吡啶（）与乙炔基苯衍生物在PdCl(PPh)-CuI作为催化剂存在下反应，通过分子内双硅烷化反应得到相应的吡啶稠合硅杂环戊二烯（-）。还进行了密度泛函理论（DFT）计算以了解反应机理。本文首次报道了钯催化剂在炔烃与二硅烷的双硅烷化反应中的成功应用。
