In the last years, among unsatured compounds, ynamides have emerged a versatile building block, becoming a widely exploited starting material in organic synthesis. This class of molecules is characterized by the presence of a nitrogen atom directly connected to a C-sp of an alkyne. As consequence, a strong polarization of the triple bond is observed, enabling a reactivity characterized by high level of regio- and/or steroselection. Recently, gold-catalysts have been employed in reactions involving ynamides in particular for the synthesis of heterocycles. In fact, after activation of the triple bond by the gold species, nucleophilic attack, usually on the Cα, is favored with the formation of a vinyl-gold intermediate that can evolve in other transformations. Thus, in accordance to our interest in gold-catalyzed functionalization on indole ring, we decided to test the possibility of using a simple 3-substituted indole as nucleophile in the reaction with an ynamide. The reaction, conducted in the presence of a gold(I) catalyst led to (Z)-(3-methyl-indol-2-yl)-2-vinyl benzensulfonamide as product.

Gold-Catalyzed cis-Hydroarylation reactions of Ynamides with Indoles: Regio- and Stereoselective synthesis of a new class of 2-vinylindoles / V. Pirovano, M. Negrato, G. Abbiati, M. Dell’Acqua, E. Rossi. ((Intervento presentato al 11. convegno Symposium on Organic Chemistry tenutosi a San Sebastian nel 2016.

Gold-Catalyzed cis-Hydroarylation reactions of Ynamides with Indoles: Regio- and Stereoselective synthesis of a new class of 2-vinylindoles

V. Pirovano
Primo
;
G. Abbiati;M. Dell’Acqua
Penultimo
;
E. Rossi
2016

Abstract

In the last years, among unsatured compounds, ynamides have emerged a versatile building block, becoming a widely exploited starting material in organic synthesis. This class of molecules is characterized by the presence of a nitrogen atom directly connected to a C-sp of an alkyne. As consequence, a strong polarization of the triple bond is observed, enabling a reactivity characterized by high level of regio- and/or steroselection. Recently, gold-catalysts have been employed in reactions involving ynamides in particular for the synthesis of heterocycles. In fact, after activation of the triple bond by the gold species, nucleophilic attack, usually on the Cα, is favored with the formation of a vinyl-gold intermediate that can evolve in other transformations. Thus, in accordance to our interest in gold-catalyzed functionalization on indole ring, we decided to test the possibility of using a simple 3-substituted indole as nucleophile in the reaction with an ynamide. The reaction, conducted in the presence of a gold(I) catalyst led to (Z)-(3-methyl-indol-2-yl)-2-vinyl benzensulfonamide as product.
gold, homogeneous catalysis, indoles, heterocycles, organic synthesis
Settore CHIM/06 - Chimica Organica
Società Chimica Italiana, Real Sociedad Espanola de Quimica
Gold-Catalyzed cis-Hydroarylation reactions of Ynamides with Indoles: Regio- and Stereoselective synthesis of a new class of 2-vinylindoles / V. Pirovano, M. Negrato, G. Abbiati, M. Dell’Acqua, E. Rossi. ((Intervento presentato al 11. convegno Symposium on Organic Chemistry tenutosi a San Sebastian nel 2016.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/422824
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