Copper catalysed azide-alkyne cycloaddition (CuAAC) in liquid ammonia.

Pengju Ji, John Atherton, Michael Page

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Copper(I) catalysed azide–alkyne cycloaddition reactions (CuAAC) occur smoothly in liquid ammonia (LNH3) at room temperature to give exclusively 1,4-substituted 1,2,3-triazoles with excellent yields (up to 99%). The CuAAC reactions in liquid ammonia require relatively small amounts of copper(I) catalyst (0.5 mole%) compared with that in conventional solvents. The product can be obtained conveniently by simply evaporation of ammonia, indicating its potential application in industry. The rate of the CuAAC reaction in liquid ammonia shows a second order dependence on the copper(I) concentration and the reaction occurs only with terminal alkynes. Deuterium exchange experiments with phenyl acetylene-d1 show that the acidity of the alkyne is increased at least 1000-fold with catalytic amounts of copper(I) in liquid ammonia. The mechanism of the CuAAC reaction in liquid ammonia is discussed.
Original languageEnglish
Pages (from-to)7965-7969
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume10
DOIs
Publication statusPublished - 23 Aug 2012

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liquid ammonia
Alkynes
Azides
Cycloaddition
Cycloaddition Reaction
cycloaddition
alkynes
Ammonia
Copper
copper
Liquids
Triazoles
acidity
acetylene
Deuterium
deuterium
ammonia
Acidity
industries
evaporation

Cite this

Ji, Pengju ; Atherton, John ; Page, Michael. / Copper catalysed azide-alkyne cycloaddition (CuAAC) in liquid ammonia. In: Organic and Biomolecular Chemistry. 2012 ; Vol. 10. pp. 7965-7969 .
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Copper catalysed azide-alkyne cycloaddition (CuAAC) in liquid ammonia. / Ji, Pengju; Atherton, John; Page, Michael.

In: Organic and Biomolecular Chemistry, Vol. 10, 23.08.2012, p. 7965-7969 .

Research output: Contribution to journalArticle

TY - JOUR

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AU - Page, Michael

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AB - Copper(I) catalysed azide–alkyne cycloaddition reactions (CuAAC) occur smoothly in liquid ammonia (LNH3) at room temperature to give exclusively 1,4-substituted 1,2,3-triazoles with excellent yields (up to 99%). The CuAAC reactions in liquid ammonia require relatively small amounts of copper(I) catalyst (0.5 mole%) compared with that in conventional solvents. The product can be obtained conveniently by simply evaporation of ammonia, indicating its potential application in industry. The rate of the CuAAC reaction in liquid ammonia shows a second order dependence on the copper(I) concentration and the reaction occurs only with terminal alkynes. Deuterium exchange experiments with phenyl acetylene-d1 show that the acidity of the alkyne is increased at least 1000-fold with catalytic amounts of copper(I) in liquid ammonia. The mechanism of the CuAAC reaction in liquid ammonia is discussed.

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