Palladium-Catalyzed Oxidative Aminocarbonylation of Alkynols

Pierluigi Plastina; Bartolo Gabriele; Giuseppe Salerno

doi:10.1055/s-2007-983828

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Synthesis 2007(19): 3083-3087
DOI: 10.1055/s-2007-983828

PSP

Palladium-Catalyzed Oxidative Aminocarbonylation of Alkynols

Pierluigi Plastina*^a, Bartolo Gabriele*^b, Giuseppe Salerno^a
^a Dipartimento di Chimica, Università della Calabria, 87036 Arcavacata di Rende, Cosenza, Italy
Fax: +39(0984)492044; e-Mail: p.plastina@unical.it;
^b Dipartimento di Scienze Farmaceutiche, Università della Calabria, 87036 Arcavacata di Rende, Cosenza, Italy
e-Mail: b.gabriele@unical.it;

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Publication History

Received 2 March 2007
Publication Date:
30 July 2007 (online)

Abstract
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Abstract

Alkynols undergo palladium-catalyzed aminocarbonylation leading to the direct formation of different heterocyclic derivatives, depending on the position of the OH group with respect to the triple bond. In the cases of 4-yn-1-ols and (Z)-2-en-4-yn-1-ols, the initially formed 2-ynamide intermediates, respectively, undergo cyclization leading to tetrahydrofuran derivatives or 2-furan-2-ylacetamides, respectively. In the case of 2-yn-1-ols, the aminocarbonylation products undergo intermolecular conjugate addition, followed by lactonization, leading to aminofuranones.

Key words

aminocarbonylation - carbonylations - cyclization - heterocycles - palladium

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