Synthesis of Borylcyclopropanes by Chromium-Promoted Cyclopropanation of Unactivated Alkenes

Masahito Murai; Chisato Mizuta; Ryuji Taniguchi; Kazuhiko Takai

doi:10.1021/acs.orglett.7b02956

Synthesis of Borylcyclopropanes by Chromium-Promoted Cyclopropanation of Unactivated Alkenes

Masahito Murai, Chisato Mizuta, Ryuji Taniguchi, Kazuhiko Takai

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

28 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 language	English
Pages (from-to)	6104-6107
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.7b02956
Publication status	Published - Nov 17 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of Borylcyclopropanes by Chromium-Promoted Cyclopropanation of Unactivated Alkenes",

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.",

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

note = "Funding Information: This work is financially supported by a Grant-in-Aid (No. 26248030) from MEXT, Japan, and MEXT program for promoting the enhancement of research universities. The authors gratefully thank Mr. Masato Kodera and Ms. Seina Ishihara (Okayama University) for HRMS measurements. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b02956",

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T1 - Synthesis of Borylcyclopropanes by Chromium-Promoted Cyclopropanation of Unactivated Alkenes

AU - Murai, Masahito

AU - Mizuta, Chisato

AU - Taniguchi, Ryuji

AU - Takai, Kazuhiko

N1 - Funding Information: This work is financially supported by a Grant-in-Aid (No. 26248030) from MEXT, Japan, and MEXT program for promoting the enhancement of research universities. The authors gratefully thank Mr. Masato Kodera and Ms. Seina Ishihara (Okayama University) for HRMS measurements. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/11/17

Y1 - 2017/11/17

N2 - 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.

AB - 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.

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Synthesis of Borylcyclopropanes by Chromium-Promoted Cyclopropanation of Unactivated Alkenes

Abstract

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