Toward a protecting-group-free halogen-metal exchange reaction: Practical, chemoselective metalation of functionalized aromatic halides using dianion-type zincate,tBu4ZnLi2

Masanobu Uchiyama, Taniyuki Furuyama, Minoru Kobayashi, Yotaro Matsumoto, Kentaro Tanaka

Research output: Contribution to journalArticlepeer-review

109 Citations (Scopus)

Abstract

A versatile preparation method for aromatic zincate compounds through a halogen-zinc exchange reaction using dilithium tetra-tert-butylzincate (tBu4ZnLi2) has been developed. This reagent permits efficient preparation of highly functionalized aromatic zincates, particularly, those with electrophilic functional groups, such as ester, amide, alcohol, and phenol. Halogen-zinc exchange reactions followed by electrophilic trapping (with allyl bromide or benzaldehyde) proved to be a powerful tool for C-C bond formation on functionalized aromatic rings. The functionalized aromatic zincate intermediate was also found to undergo copper- and palladium-catalyzed C-C bond-forming reactions with good yields and high chemoselectivity.

Original languageEnglish
Pages (from-to)8404-8405
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number26
DOIs
Publication statusPublished - 2006 Jul 5

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Toward a protecting-group-free halogen-metal exchange reaction: Practical, chemoselective metalation of functionalized aromatic halides using dianion-type zincate,<sup>t</sup>Bu<sub>4</sub>ZnLi<sub>2</sub>'. Together they form a unique fingerprint.

Cite this