TY - JOUR
T1 - Palladium-catalyzed Ci-H fluorosilylation of 2-phenylpyridines
T2 - Synthesis of silafluorene equivalents
AU - Xiao, Qing
AU - Meng, Xiangtai
AU - Kanai, Motomu
AU - Kuninobu, Yoichiro
PY - 2014/3/17
Y1 - 2014/3/17
N2 - 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 Ci-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. 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 Ci-H fluorosilylation. A Lewis acid-base interaction exists between the silicon and nitrogen atoms, and the obtained fluorosilylated products can be regarded as silafluorene equivalents.
AB - 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 Ci-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. 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 Ci-H fluorosilylation. A Lewis acid-base interaction exists between the silicon and nitrogen atoms, and the obtained fluorosilylated products can be regarded as silafluorene equivalents.
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U2 - 10.1002/anie.201310293
DO - 10.1002/anie.201310293
M3 - Article
C2 - 24633971
AN - SCOPUS:84896362209
SN - 1433-7851
VL - 53
SP - 3168
EP - 3172
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 12
ER -