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Palladium‐Catalyzed CH Fluorosilylation of 2‐Phenylpyridines: Synthesis of Silafluorene Equivalents
Author(s) -
Xiao Qing,
Meng Xiangtai,
Kanai Motomu,
Kuninobu Yoichiro
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201310293
Subject(s) - palladium , catalysis , chemistry , crystal structure , equivalent , lewis acids and bases , derivative (finance) , silicon , nitrogen , palladium catalyst , base (topology) , single crystal , fluorescence , medicinal chemistry , stereochemistry , organic chemistry , crystallography , biochemistry , physics , quantum mechanics , financial economics , economics , mathematical analysis , mathematics
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 CH 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.