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

34 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

Access to Document

10.1016/j.jorganchem.2006.06.047

Cite this

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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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.",

keywords = "Chromium(II), Cyclopropane, Cyclopropylsilane",

author = "Kazuhiko Takai and Shota Toshikawa and Atsushi Inoue and Ryo Kokumai and Masato Hirano",

note = "Funding Information: Financial support by a Grant-in-Aid for Scientific Research on Priority Areas (No. 14078219, “Reaction Control of Dynamic Complexes”) from the Ministry of Education, Culture, Sports, Science and Technology of Japan, and Nagase Science Foundation are gratefully acknowledged.",

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AU - Takai, Kazuhiko

AU - Toshikawa, Shota

AU - Inoue, Atsushi

AU - Kokumai, Ryo

AU - Hirano, Masato

N1 - Funding Information: Financial support by a Grant-in-Aid for Scientific Research on Priority Areas (No. 14078219, “Reaction Control of Dynamic Complexes”) from the Ministry of Education, Culture, Sports, Science and Technology of Japan, and Nagase Science Foundation are gratefully acknowledged.

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N2 - 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.

AB - 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.

KW - Chromium(II)

KW - Cyclopropane

KW - Cyclopropylsilane

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