One-pot transformation of RCHO to (E)-RCH=CHSiMe3 using CHI3, Mn, Me3SiCl, and a catalytic amount of CrCl2

Kazuhiko Takai; Shintaro Hikasa; Tetsuya Ichiguchi; Naoki Sumino

doi:10.1055/s-1999-2948

One-pot transformation of RCHO to (E)-RCH=CHSiMe₃ using CHI₃, Mn, Me₃SiCl, and a catalytic amount of CrCl₂

Kazuhiko Takai, Shintaro Hikasa, Tetsuya Ichiguchi, Naoki Sumino

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

20 Citations (Scopus)

Abstract

Iodoform is reduced with manganese in the presence of Me₃SiCl to give Me₃SiCHI₂ (1). A one-pot transformation of aldehydes to (E)-1- alkenyltrimethylsilanes is then performed with iodoform, manganese, Me₂SiCl, and a catalytic amount of chromium(II) chloride in THF via in situ formation of 1.

Original language	English
Pages (from-to)	1769-1771
Number of pages	3
Journal	Synlett
Issue number	11
DOIs	https://doi.org/10.1055/s-1999-2948
Publication status	Published - Jan 1 1999

Keywords

(E)-1- alkenylsilane
Chromium(II)
Chromium(III)
Geminal dichromium reagent
Geminal diiodo compound
Manganese

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-1999-2948

Cite this

@article{f1069df7e1104b8b885921b87af1ac4a,

title = "One-pot transformation of RCHO to (E)-RCH=CHSiMe3 using CHI3, Mn, Me3SiCl, and a catalytic amount of CrCl2",

abstract = "Iodoform is reduced with manganese in the presence of Me3SiCl to give Me3SiCHI2 (1). A one-pot transformation of aldehydes to (E)-1- alkenyltrimethylsilanes is then performed with iodoform, manganese, Me2SiCl, and a catalytic amount of chromium(II) chloride in THF via in situ formation of 1.",

keywords = "(E)-1- alkenylsilane, Chromium(II), Chromium(III), Geminal dichromium reagent, Geminal diiodo compound, Manganese",

author = "Kazuhiko Takai and Shintaro Hikasa and Tetsuya Ichiguchi and Naoki Sumino",

year = "1999",

month = jan,

day = "1",

doi = "10.1055/s-1999-2948",

language = "English",

pages = "1769--1771",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "11",

}

TY - JOUR

T1 - One-pot transformation of RCHO to (E)-RCH=CHSiMe3 using CHI3, Mn, Me3SiCl, and a catalytic amount of CrCl2

AU - Takai, Kazuhiko

AU - Hikasa, Shintaro

AU - Ichiguchi, Tetsuya

AU - Sumino, Naoki

PY - 1999/1/1

Y1 - 1999/1/1

N2 - Iodoform is reduced with manganese in the presence of Me3SiCl to give Me3SiCHI2 (1). A one-pot transformation of aldehydes to (E)-1- alkenyltrimethylsilanes is then performed with iodoform, manganese, Me2SiCl, and a catalytic amount of chromium(II) chloride in THF via in situ formation of 1.

AB - Iodoform is reduced with manganese in the presence of Me3SiCl to give Me3SiCHI2 (1). A one-pot transformation of aldehydes to (E)-1- alkenyltrimethylsilanes is then performed with iodoform, manganese, Me2SiCl, and a catalytic amount of chromium(II) chloride in THF via in situ formation of 1.

KW - (E)-1- alkenylsilane

KW - Chromium(II)

KW - Chromium(III)

KW - Geminal dichromium reagent

KW - Geminal diiodo compound

KW - Manganese

UR - http://www.scopus.com/inward/record.url?scp=0032706458&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032706458&partnerID=8YFLogxK

U2 - 10.1055/s-1999-2948

DO - 10.1055/s-1999-2948

M3 - Article

AN - SCOPUS:0032706458

SN - 0936-5214

SP - 1769

EP - 1771

JO - Synlett

JF - Synlett

IS - 11

ER -