Development of highly chemoselective bulky zincate complex, tBu 4ZnLi2: Design, structure, and practical applications in small-/macromolecular synthesis

Taniyuki Furayama, Mitsuhiro Yonehara, Sho Arimoto, Minoru Kobayashi, Yotaro Matsumoto, Masanobu Uchiyama

Research output: Contribution to journalArticle

65 Citations (Scopus)

Abstract

We present full details of the unique reactivities of the newly developed dianion-type bulky zincate, dilithium tetra-ferf-butylzincate (tBu 4ZnLi2). With this reagent, halogen-zinc exchange reaction of variously functionalized haloaromatics and anionic polymerization of N-isopropylacrylamide (NIPAm)/styrene with excellent chemoselectivity were realized. Halogen-zinc exchange reaction followed by electrophilic trapping with propargyl bromide provided a convenient route to functionalized phenylallenes, particularly those with electrophilic functional groups (such as cyano, amide and halogens). Spectral and computational studies of the structure in the gas and liquid phases indicated extraordinary stabilization of this dianion-type zincate by its bulky ligands.

Original languageEnglish
Pages (from-to)10348-10356
Number of pages9
JournalChemistry - A European Journal
Volume14
Issue number33
DOIs
Publication statusPublished - 2008 Nov 17

Keywords

  • Chemoselective metalation
  • Halogen-metal exchange
  • Nucleophilic substitution polymerization
  • Zinc

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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