钯催化 2-苯基吡啶的 C-H 氟硅基化反应：硅芴酮等价物的合成。

Palladium-catalyzed C-H fluorosilylation of 2-phenylpyridines: synthesis of silafluorene equivalents.

机构信息

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).

出版信息

Angew Chem Int Ed Engl. 2014 Mar 17;53(12):3168-72. doi: 10.1002/anie.201310293.

DOI:10.1002/anie.201310293

PMID:24633971

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.

摘要

用氨基（1,3,2-二氧硼杂环戊烷-2-基）二苯基硅烷处理 2-苯基吡啶，在钯催化下得到了产率良好到优秀的氟硅基化 2-苯基吡啶。这是首例 C-H 氟硅基化反应。单晶 X 射线结构分析揭示了硅原子和氮原子之间的路易斯酸碱相互作用，得到的氟硅基化产物是硅芴等价物。氟硅基化产物的荧光强度强于相应的硅芴衍生物。