New formulas for organozincate chemistry

Masanobu Uchiyama, Mitsuyoshi Kameda, Osamu Mishima, Nobuko Yokoyama, Minako Koike, Yoshinori Kondo, Takao Sakamoto

Research output: Contribution to journalArticle

164 Citations (Scopus)

Abstract

As a new type of zincate, we designed various new organozinc derivatives, Me3Zn(R)Li2 (R = Me, CN, SCN), which could be prepared in situ from lithium trimethylzincate and anion species such as methyllithium, lithium cyanide, and lithium thiocyanate. We investigated the reactivities of these zincates toward the halogen (or tellurium)-zinc exchange, Michael addition, carbozincation, and epoxide ring opening reactions. On the basis of their excellent chemical yields and chemoselectivities, these species were considered to be differentiated from ordinary triorganozincates, R3ZnLi. We also discuss the structure of the newly designed zincates using 1H NMR/Raman/in situ FTIR/extended X-ray absorption the structure (EXAFS) spectroscopic and the density functional theory (DFT) theoretical studies. All results strongly support the fact that these newly designed zincates are a new category of zincate species. This observation is also identical with the fact that newly designed zincates have a higher and unique reactivity compared to the conventional triorganozincates.

Original languageEnglish
Pages (from-to)4934-4946
Number of pages13
JournalJournal of the American Chemical Society
Volume120
Issue number20
DOIs
Publication statusPublished - 1998 May 27

ASJC Scopus subject areas

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

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    Uchiyama, M., Kameda, M., Mishima, O., Yokoyama, N., Koike, M., Kondo, Y., & Sakamoto, T. (1998). New formulas for organozincate chemistry. Journal of the American Chemical Society, 120(20), 4934-4946. https://doi.org/10.1021/ja973855t