Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 12, Pages 3168-3172Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310293
Keywords
CH activation; fluorescence; heterocycles; palladium; silicon
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Funding
- ERATO from JST
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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.
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