Reaction of alkynylsilanes with CuCl in polar solvents leading to alkynyl group transfer from Si to Cu

Yasushi Nishihara; Miwa Takemura; Atsunori Mori; Kohtaro Osakada

doi:10.1016/S0022-328X(00)00794-4

Reaction of alkynylsilanes with CuCl in polar solvents leading to alkynyl group transfer from Si to Cu

Yasushi Nishihara, Miwa Takemura, Atsunori Mori, Kohtaro Osakada

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

39 Citations (Scopus)

Abstract

The reaction of 1-phenyl-2-trimethylsilylethyne with CuCl at 80-100°C in N,N-dimethylformamide (DMF) or N,N-dimethylimidazolidinone (DMI) yielded the alkynylcopper species [Cu₂Cl(C≡CPh)]_n (1) in 56-63% yields. Heating 1 at 80°C under aerobic conditions gave 1,4-diphenyl-1,3-butadiyne in 82% yield via an oxidative coupling of the phenylethynyl ligands.

Original language	English
Pages (from-to)	282-286
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	620
Issue number	1-2
DOIs	https://doi.org/10.1016/S0022-328X(00)00794-4
Publication status	Published - Feb 15 2001
Externally published	Yes

Keywords

Alkynylsilane
Copper salt
Diyne
Oxidative coupling
Transmetalation

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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title = "Reaction of alkynylsilanes with CuCl in polar solvents leading to alkynyl group transfer from Si to Cu",

abstract = "The reaction of 1-phenyl-2-trimethylsilylethyne with CuCl at 80-100°C in N,N-dimethylformamide (DMF) or N,N-dimethylimidazolidinone (DMI) yielded the alkynylcopper species [Cu2Cl(C≡CPh)]n (1) in 56-63% yields. Heating 1 at 80°C under aerobic conditions gave 1,4-diphenyl-1,3-butadiyne in 82% yield via an oxidative coupling of the phenylethynyl ligands.",

keywords = "Alkynylsilane, Copper salt, Diyne, Oxidative coupling, Transmetalation",

author = "Yasushi Nishihara and Miwa Takemura and Atsunori Mori and Kohtaro Osakada",

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T1 - Reaction of alkynylsilanes with CuCl in polar solvents leading to alkynyl group transfer from Si to Cu

AU - Nishihara, Yasushi

AU - Takemura, Miwa

AU - Mori, Atsunori

AU - Osakada, Kohtaro

PY - 2001/2/15

Y1 - 2001/2/15

N2 - The reaction of 1-phenyl-2-trimethylsilylethyne with CuCl at 80-100°C in N,N-dimethylformamide (DMF) or N,N-dimethylimidazolidinone (DMI) yielded the alkynylcopper species [Cu2Cl(C≡CPh)]n (1) in 56-63% yields. Heating 1 at 80°C under aerobic conditions gave 1,4-diphenyl-1,3-butadiyne in 82% yield via an oxidative coupling of the phenylethynyl ligands.

AB - The reaction of 1-phenyl-2-trimethylsilylethyne with CuCl at 80-100°C in N,N-dimethylformamide (DMF) or N,N-dimethylimidazolidinone (DMI) yielded the alkynylcopper species [Cu2Cl(C≡CPh)]n (1) in 56-63% yields. Heating 1 at 80°C under aerobic conditions gave 1,4-diphenyl-1,3-butadiyne in 82% yield via an oxidative coupling of the phenylethynyl ligands.

KW - Alkynylsilane

KW - Copper salt

KW - Diyne

KW - Oxidative coupling

KW - Transmetalation

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DO - 10.1016/S0022-328X(00)00794-4

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