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

34 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

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Palladium
Catalysis
Nitrogen
Lewis Acids
Silicon
Atoms
Acids
Fluorescence
Single crystals
Derivatives
X rays
2-phenylpyridine

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Palladium-catalyzed Ci-H fluorosilylation of 2-phenylpyridines : Synthesis of silafluorene equivalents. / Xiao, Qing; Meng, Xiangtai; Kanai, Motomu; Kuninobu, Yoichiro.

In: Angewandte Chemie - International Edition, Vol. 53, No. 12, 17.03.2014, p. 3168-3172.

Research output: Contribution to journalArticle

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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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