Chemoselective Metalation of Functionalized Organic Halides Using Ate Complexes

Yoshinori Kondo, Masanobu Uchiyama, Takao Sakamoto

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Ate complexes have been used for selective carbon-carbon bond forming reactions, however access to ate complexes with electrophilic functional groups has been limited. Main reason for the limitation lies on the preparative method of ate complexes, which includes usage of highly reactive organolithium and organomagnesium reagents. In order to develop a new strategy for the preparation of ate complexes directly from other ate complexes, we investigated halogen-metal exchange reactions of organic halides with ate complexes. The metalation is considered to be potentially chemoselective and wide spectrum of application in organic synthesis is expected. Cuprates and zincates turned out to be excellent metalating reagents of functionalized aryl and alkyl halides. Some chemoselective transformations were achieved using the metalation with ate complexes and modified zincates showed very specific reactivity toward intramolecular epoxide opening reaction.

Original languageEnglish
Pages (from-to)547-556
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume55
Issue number6
DOIs
Publication statusPublished - 1997 Jan 1

Keywords

  • Ate complex
  • Baldwin's rule
  • Cc-1065/duocarmycin pharmacophore
  • Chemoselectivity
  • Cuprate
  • Halogen-metal exchange reaction
  • Intramolecular epoxide opening
  • Zincate

ASJC Scopus subject areas

  • Organic Chemistry

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