Catalytic activation of silylated nucleophiles using tBu-P4 as a base

Masahiro Ueno, Chieko Hori, Koichi Suzawa, Masashi Ebisawa, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

51 Citations (Scopus)

Abstract

Trialkylsilyl groups play an important role as effective protecting groups in organic synthesis. Various O, N, and C nucleophilic sites can be protected by trialkylsilyl groups to control the selectivity of reactions. The nucleophilic attack of a fluoride anion on a silyl group is recognized as one of the most useful methods for desilylation. The activation of the nucleophile-silicon bond is important not only for desilylation but also for the generation of a reactive nucleophilic anion to achieve a new bond formation. The phosphazene bases developed by Schwesinger are known to be strong non-metallic organic bases. Among them, the tBu-P4 base has been used for various selective deprotonative transformations, although the ability of tBu-P4 base to activate silylated nucleophiles has not yet been shown. A novel catalytic activation of various O, N, and C nucleophile-silicon bonds using tBu-P4 base was investigated to perform nucleophilic reactions with various electrophiles.

Original languageEnglish
Pages (from-to)1965-1968
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number10
DOIs
Publication statusPublished - 2005 May 13

Keywords

  • Anions
  • Aromatic compounds
  • Catalysis
  • Phosphazenes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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