One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles

Trond V. Hansen; Peng Wu; Valery V. Fokin

doi:10.1021/jo050163b

One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles

Trond V. Hansen, Peng Wu, Valery V. Fokin

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242 Scopus citations

Abstract

3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional groups do not interfere with the reaction, which can be performed in aqueous solvents without protection from oxygen. Since all reagents are used in stoichiometric amounts, formation of byproducts is minimized.

Original language	English (US)
Pages (from-to)	7761-7764
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	70
Issue number	19
DOIs	https://doi.org/10.1021/jo050163b
State	Published - Sep 16 2005
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles",

abstract = "3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional groups do not interfere with the reaction, which can be performed in aqueous solvents without protection from oxygen. Since all reagents are used in stoichiometric amounts, formation of byproducts is minimized.",

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year = "2005",

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AU - Hansen, Trond V.

AU - Wu, Peng

AU - Fokin, Valery V.

PY - 2005/9/16

Y1 - 2005/9/16

N2 - 3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional groups do not interfere with the reaction, which can be performed in aqueous solvents without protection from oxygen. Since all reagents are used in stoichiometric amounts, formation of byproducts is minimized.

AB - 3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional groups do not interfere with the reaction, which can be performed in aqueous solvents without protection from oxygen. Since all reagents are used in stoichiometric amounts, formation of byproducts is minimized.

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JO - Journal of Organic Chemistry

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One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles

Abstract

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