Organic synthesis using organic superbase

Yoshinori Kondo, Masahiro Ueno, Yoshiyuki Tanaka

Research output: Contribution to journalReview articlepeer-review

15 Citations (Scopus)

Abstract

Organic bases are important class of reagents for synthetic chemistry. Recent developments in optimizing the basicity and in reducing nucleophilicity provide various new synthetic methodologies. This review describes synthetic applications of two excellent organic superbases. One is phosphazene base developed by Schwesinger and the other is proazaphosphatrane base, which was first synthesized by Verkade. The bacisity of the Schwesinger's P 4 base is in the range of organolithium bases and 18 orders of magnitude more basic than conventional DBU. Verkade bases are also strong bases due to the protonation on the bridgehead phosphorus atom with a resultant transannulation to form the corresponding azaphosphatrane structure. Properties, applications, and synthetic benefits of these bases are discussed.

Original languageEnglish
Pages (from-to)453-463
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume63
Issue number5
DOIs
Publication statusPublished - 2005 May

Keywords

  • Basicity
  • Deprotonation
  • Nucleophilicity
  • Organic base
  • Phosphazene
  • Proazaphosphatrane
  • Schwesinger base
  • Steric hindrance
  • Verkade base

ASJC Scopus subject areas

  • Organic Chemistry

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