Synthesis of Borylcyclopropanes by Chromium-Promoted Cyclopropanation of Unactivated Alkenes

Masahito Murai, Chisato Mizuta, Ryuji Taniguchi, Kazuhiko Takai

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The combination of diiodomethylboronate ester, CrCl2 with TMEDA promoted borylcyclopropanation of unactivated alkenes under mild conditions. Compared with the typical Simmons-Smith cyclopropanation, the current protocol offers the following advantages: (1) the reaction proceeds stereoselectively with disubstituted alkenes even without hydroxy or alkoxy groups; (2) both electron-rich and electron-deficient alkenes can be applicable; and (3) the reaction does not require potentially flammable alkylzinc. These unique reactivity features result from the steric and electronic nature of the gem-dichromiomethane intermediates.

Original languageEnglish
Pages (from-to)6104-6107
Number of pages4
JournalOrganic Letters
Volume19
Issue number22
DOIs
Publication statusPublished - Nov 17 2017

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Alkenes
Chromium
alkenes
chromium
synthesis
Electrons
Gems
esters
Esters
electrons
reactivity
electronics

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis of Borylcyclopropanes by Chromium-Promoted Cyclopropanation of Unactivated Alkenes. / Murai, Masahito; Mizuta, Chisato; Taniguchi, Ryuji; Takai, Kazuhiko.

In: Organic Letters, Vol. 19, No. 22, 17.11.2017, p. 6104-6107.

Research output: Contribution to journalArticle

Murai, Masahito ; Mizuta, Chisato ; Taniguchi, Ryuji ; Takai, Kazuhiko. / Synthesis of Borylcyclopropanes by Chromium-Promoted Cyclopropanation of Unactivated Alkenes. In: Organic Letters. 2017 ; Vol. 19, No. 22. pp. 6104-6107.
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