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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310293
Subject(s) - palladium , catalysis , chemistry , derivative (finance) , crystal structure , lewis acids and bases , equivalent , nitrogen , silicon , single crystal , palladium catalyst , fluorescence , stereochemistry , medicinal chemistry , organic chemistry , crystallography , biochemistry , financial economics , economics , physics , quantum mechanics
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.