Palladium-catalyzed Ci-H fluorosilylation of 2-phenylpyridines: Synthesis of silafluorene equivalents

Qing Xiao, Xiangtai Meng, Motomu Kanai, Yoichiro Kuninobu

Research output: Contribution to journalArticle

36 Citations (Scopus)

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 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.

Original languageEnglish
Pages (from-to)3168-3172
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number12
DOIs
Publication statusPublished - Mar 17 2014
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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