Chromium-Mediated Stannylcyclopropanation of Alkenes with (Diiodomethyl)stannanes

Masahito Murai; Ryuji Taniguchi; Chisato Mizuta; Kazuhiko Takai

doi:10.1021/acs.orglett.9b00658

Chromium-Mediated Stannylcyclopropanation of Alkenes with (Diiodomethyl)stannanes

Masahito Murai, Ryuji Taniguchi, Chisato Mizuta, Kazuhiko Takai

School of Engineering

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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 language	English
Pages (from-to)	2668-2672
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.9b00658
Publication status	Published - Apr 19 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Chromium-Mediated Stannylcyclopropanation of Alkenes with (Diiodomethyl)stannanes",

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. ",

author = "Masahito Murai and Ryuji Taniguchi and Chisato Mizuta and Kazuhiko Takai",

note = "Funding Information: This work was financially supported by Grant-in-Aid for Scientific Research (A) (No. 18H03911) from MEXT, Japan. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.9b00658",

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T1 - Chromium-Mediated Stannylcyclopropanation of Alkenes with (Diiodomethyl)stannanes

AU - Murai, Masahito

AU - Taniguchi, Ryuji

AU - Mizuta, Chisato

AU - Takai, Kazuhiko

N1 - Funding Information: This work was financially supported by Grant-in-Aid for Scientific Research (A) (No. 18H03911) from MEXT, Japan. Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/4/19

Y1 - 2019/4/19

N2 - 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.

AB - 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.

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Chromium-Mediated Stannylcyclopropanation of Alkenes with (Diiodomethyl)stannanes

Abstract

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