Heterosubstituted cyclopropanation of alkenes with organochromium reagents derived from heterosubstituted dihalomethanes, CrCl2, and tetraalkylethylenediamine

Kazuhiko Takai; Shota Toshikawa; Atsushi Inoue; Ryo Kokumai; Masato Hirano

doi:10.1016/j.jorganchem.2006.06.047

Heterosubstituted cyclopropanation of alkenes with organochromium reagents derived from heterosubstituted dihalomethanes, CrCl₂, and tetraalkylethylenediamine

Kazuhiko Takai, Shota Toshikawa, Atsushi Inoue, Ryo Kokumai, Masato Hirano

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

32 Citations (Scopus)

Abstract

Iodocyclopropanes of trans configuration are produced stereoselectively from terminal alkenes by treatment with a reagent derived from iodoform, chromium(II) chloride, and TEEDA (N,N,N′,N′-tetraethylethylenediamine) in THF. Similarly, cyclopropylsilanes and cyclopropylboronic esters are obtained by using R₃SiCHI₂, and a combination of Cl₂CHB(OR)₂ and LiI instead of iodoform, respectively. The heterocyclopropanation occurs selectively at terminal double bonds, and di- and trisubstituted double bonds in the same molecules remain unchanged. Such functional groups as alcohol, ether, silyl ether, ester, tertiary amine, and amide groups are compatible with the reaction conditions.

Original language	English
Pages (from-to)	520-529
Number of pages	10
Journal	Journal of Organometallic Chemistry
Volume	692
Issue number	1-3
DOIs	https://doi.org/10.1016/j.jorganchem.2006.06.047
Publication status	Published - Jan 1 2007

Keywords

Chromium(II)
Cyclopropane
Cyclopropylsilane

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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Heterosubstituted cyclopropanation of alkenes with organochromium reagents derived from heterosubstituted dihalomethanes, CrCl₂, and tetraalkylethylenediamine. / Takai, Kazuhiko; Toshikawa, Shota; Inoue, Atsushi; Kokumai, Ryo; Hirano, Masato.

In: Journal of Organometallic Chemistry, Vol. 692, No. 1-3, 01.01.2007, p. 520-529.

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

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AU - Kokumai, Ryo

AU - Hirano, Masato

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