We report herein the first example of the silver triflate catalysed synthesis of 1,3-dicarbo-substituted isochromene derivatives starting from 2-alkynyl(hetero)arylaldehydes and enolizable ketones. The reaction proceeds in a cascade fashion under mild heating with complete regioselectivity and moderate-to-good yields. In some cases, the reaction gives unexpected homodimeric products. Two competitive mechanistic paths for the formation of the desired isochromene derivatives and the homodimeric products are described.

Silver Catalyzed Domino Approach to 1,3-Dicarbosubstituted Isochromenes / M. Dell'Acqua, V. Pirovano, S. Peroni, G. Tseberlidis, D. Nava, E. Rossi, G. Abbiati. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2017:11(2017 Mar 21), pp. 1425-1433. [10.1002/ejoc.201601602]

Silver Catalyzed Domino Approach to 1,3-Dicarbosubstituted Isochromenes

M. Dell'Acqua
Primo
;
V. Pirovano
Secondo
;
G. Tseberlidis;D. Nava;E. Rossi
Penultimo
;
G. Abbiati
2017

Abstract

We report herein the first example of the silver triflate catalysed synthesis of 1,3-dicarbo-substituted isochromene derivatives starting from 2-alkynyl(hetero)arylaldehydes and enolizable ketones. The reaction proceeds in a cascade fashion under mild heating with complete regioselectivity and moderate-to-good yields. In some cases, the reaction gives unexpected homodimeric products. Two competitive mechanistic paths for the formation of the desired isochromene derivatives and the homodimeric products are described.
isochromenes; alkynes; isochromenylium; domino reaction; silver
Settore CHIM/06 - Chimica Organica
21-mar-2017
gen-2017
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/487031
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