title: Palladium-catalyzed C-H fluorosilylation of 2-phenylpyridines: synthesis of silafluorene equivalents.
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.
authors.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).
authors.forename: Qing
authors.initials: Q
authors.lastname: Xiao
authors.forename: Xiangtai
authors.initials: X
authors.lastname: Meng
authors.forename: Motomu
authors.initials: M
authors.lastname: Kanai
authors.forename: Yoichiro
authors.initials: Y
authors.lastname: Kuninobu
mesh_terms: D002384:Catalysis; D003500:Cyclization; D005453:Fluorescence; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*
chemical_list: D010165:Palladium; D012825:Silicon
keywords: CH activation; fluorescence; heterocycles; palladium; silicon