Chromium-Mediated Stannylcyclopropanation of Alkenes with (Diiodomethyl)stannanes

Masahito Murai, Ryuji Taniguchi, Chisato Mizuta, Kazuhiko Takai

Research output: Contribution to journalArticle

Abstract

A stannyl-group-substituted gem-dichromiomethane species, generated in situ from CrCl 2 , TMEDA, and tributyl(diiodomethyl)stannane, worked as an efficient stannylcarbene equivalent to promote cyclopropanation of alkenes. The reaction provided synthetically useful stannylcyclopropanes directly from commercially available unactivated alkenes without using potentially flammable alkylzinc and diazo compounds. Structural characterization of stannyl- and germyl-group-substituted gem-dichromiomethane complexes and the effect of group 14 elements containing substituents for cyclopropanation are also described.

Original languageEnglish
Pages (from-to)2668-2672
Number of pages5
JournalOrganic Letters
Volume21
Issue number8
DOIs
Publication statusPublished - Apr 19 2019

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Gems
Alkenes
Chromium
alkenes
chromium
stannane
phenyllithium

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Chromium-Mediated Stannylcyclopropanation of Alkenes with (Diiodomethyl)stannanes. / Murai, Masahito; Taniguchi, Ryuji; Mizuta, Chisato; Takai, Kazuhiko.

In: Organic Letters, Vol. 21, No. 8, 19.04.2019, p. 2668-2672.

Research output: Contribution to journalArticle

Murai, Masahito ; Taniguchi, Ryuji ; Mizuta, Chisato ; Takai, Kazuhiko. / Chromium-Mediated Stannylcyclopropanation of Alkenes with (Diiodomethyl)stannanes. In: Organic Letters. 2019 ; Vol. 21, No. 8. pp. 2668-2672.
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