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Issue 3, 2012
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Click-alkynylation of N- and P-nucleophiles by oxidative cross-coupling with alkynylcopper reagents: a general synthesis of ynamides and alkynylphosphonates

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Abstract

Nitrogen- and phosphorus-based nucleophiles can be smoothly transformed to the corresponding heteroatom-substituted alkynes by simple reaction at room temperature and under an oxygen atmosphere with copper acetylides. These stable, readily available, polymers act as especially efficient reagents for the introduction of an alkyne group under remarkably mild oxidative conditions which allow for their formal umpolung. Chelating ligands such as TMEDA and N-methylimidazole are efficient organic promoters, allowing for clean and fast oxidative cross-couplings, even with complex substrates.

Graphical abstract: Click-alkynylation of N- and P-nucleophiles by oxidative cross-coupling with alkynylcopper reagents: a general synthesis of ynamides and alkynylphosphonates

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Publication details

The article was received on 25 Oct 2011, accepted on 01 Dec 2011 and first published on 02 Dec 2011


Article type: Edge Article
DOI: 10.1039/C2SC00842D
Citation: Chem. Sci., 2012,3, 756-760
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    Click-alkynylation of N- and P-nucleophiles by oxidative cross-coupling with alkynylcopper reagents: a general synthesis of ynamides and alkynylphosphonates

    K. Jouvin, J. Heimburger and G. Evano, Chem. Sci., 2012, 3, 756
    DOI: 10.1039/C2SC00842D

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