Four-component coupling reactions of silylacetylenes, allyl carbonates, and trimethylsilyl azide catalyzed by a Pd(0)-Cu(I) bimetallic catalyst. Fully substituted triazole synthesis from seemingly internal alkynes

Shin Kamijo; Tetsuo Kin; Yoshinori Yamamoto

doi:10.1016/j.tetlet.2003.11.070

Four-component coupling reactions of silylacetylenes, allyl carbonates, and trimethylsilyl azide catalyzed by a Pd(0)-Cu(I) bimetallic catalyst. Fully substituted triazole synthesis from seemingly internal alkynes

Shin Kamijo, Tetsuo Kin, Yoshinori Yamamoto

SCI - Research and Analytical Center for Giant Molecules

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

58 Citations (Scopus)

Abstract

Fully substituted triazoles were synthesized via the four-component coupling reaction of unactivated silylacetylenes, two equivalents of allyl carbonates, and trimethylsilyl azide in the presence of a Pd(0)-Cu(I) bimetallic catalyst. Various trisubstituted 1,2,3-triazoles were obtained in good yields. The reaction most probably proceeds through the [3+2] cycloaddition reaction between the alkynylcopper species and azide followed by the cross-coupling reaction between the vinylcopper intermediate and π-allylpalladium complex.

Original language	English
Pages (from-to)	689-691
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2003.11.070
Publication status	Published - 2004 Jan 19

Keywords

Bimetallic catalyst
Copper catalyst
Four-component coupling
Palladium catalyst
TMS-azide
Triazole
π-Allylpalladium complex

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Four-component coupling reactions of silylacetylenes, allyl carbonates, and trimethylsilyl azide catalyzed by a Pd(0)-Cu(I) bimetallic catalyst. Fully substituted triazole synthesis from seemingly internal alkynes. / Kamijo, Shin; Kin, Tetsuo; Yamamoto, Yoshinori.

In: Tetrahedron Letters, Vol. 45, No. 4, 19.01.2004, p. 689-691.

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

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abstract = "Fully substituted triazoles were synthesized via the four-component coupling reaction of unactivated silylacetylenes, two equivalents of allyl carbonates, and trimethylsilyl azide in the presence of a Pd(0)-Cu(I) bimetallic catalyst. Various trisubstituted 1,2,3-triazoles were obtained in good yields. The reaction most probably proceeds through the [3+2] cycloaddition reaction between the alkynylcopper species and azide followed by the cross-coupling reaction between the vinylcopper intermediate and π-allylpalladium complex.",

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AU - Kamijo, Shin

AU - Kin, Tetsuo

AU - Yamamoto, Yoshinori

PY - 2004/1/19

Y1 - 2004/1/19

N2 - Fully substituted triazoles were synthesized via the four-component coupling reaction of unactivated silylacetylenes, two equivalents of allyl carbonates, and trimethylsilyl azide in the presence of a Pd(0)-Cu(I) bimetallic catalyst. Various trisubstituted 1,2,3-triazoles were obtained in good yields. The reaction most probably proceeds through the [3+2] cycloaddition reaction between the alkynylcopper species and azide followed by the cross-coupling reaction between the vinylcopper intermediate and π-allylpalladium complex.

AB - Fully substituted triazoles were synthesized via the four-component coupling reaction of unactivated silylacetylenes, two equivalents of allyl carbonates, and trimethylsilyl azide in the presence of a Pd(0)-Cu(I) bimetallic catalyst. Various trisubstituted 1,2,3-triazoles were obtained in good yields. The reaction most probably proceeds through the [3+2] cycloaddition reaction between the alkynylcopper species and azide followed by the cross-coupling reaction between the vinylcopper intermediate and π-allylpalladium complex.

KW - Bimetallic catalyst

KW - Copper catalyst

KW - Four-component coupling

KW - Palladium catalyst

KW - TMS-azide

KW - Triazole

KW - π-Allylpalladium complex

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Four-component coupling reactions of silylacetylenes, allyl carbonates, and trimethylsilyl azide catalyzed by a Pd(0)-Cu(I) bimetallic catalyst. Fully substituted triazole synthesis from seemingly internal alkynes

Abstract

Keywords

ASJC Scopus subject areas

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