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 | |
| Publication status | Published - Nov 17 2017 |
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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 journal › Article
}
TY - JOUR
T1 - Synthesis of Borylcyclopropanes by Chromium-Promoted Cyclopropanation of Unactivated Alkenes
AU - Murai, Masahito
AU - Mizuta, Chisato
AU - Taniguchi, Ryuji
AU - Takai, Kazuhiko
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.
UR - http://www.scopus.com/inward/record.url?scp=85034644809&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85034644809&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.7b02956
DO - 10.1021/acs.orglett.7b02956
M3 - Article
AN - SCOPUS:85034644809
VL - 19
SP - 6104
EP - 6107
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 22
ER -