Photocatalytic Isocyanide-Based Multicomponent Domino Cascade toward the Stereoselective Formation of Iminofurans

Sveva Pelliccia; Antonella Ilenia Alfano; Paolo Luciano; Ettore Novellino; Alberto Massarotti; Gian Cesare Tron; Davide Ravelli; Mariateresa Giustiniano

doi:10.1021/acs.joc.9b02709

Photocatalytic Isocyanide-Based Multicomponent Domino Cascade toward the Stereoselective Formation of Iminofurans

J Org Chem. 2020 Feb 21;85(4):1981-1990. doi: 10.1021/acs.joc.9b02709. Epub 2020 Jan 10.

Authors

Sveva Pelliccia¹, Antonella Ilenia Alfano¹, Paolo Luciano¹, Ettore Novellino¹, Alberto Massarotti², Gian Cesare Tron², Davide Ravelli³, Mariateresa Giustiniano¹

Affiliations

¹ Department of Pharmacy , University of Naples Federico II , via D. Montesano 49 , 80131 , Napoli , Italy.
² Department of Pharmaceutical Sciences , University of Piemonte Orientale , Largo Donegani 2 , 28100 , Novara , Italy.
³ PhotoGreen Lab, Department of Chemistry , University of Pavia , Viale Taramelli 12 , 27100 , Pavia , Italy.

PMID: 31880934
DOI: 10.1021/acs.joc.9b02709

Abstract

A visible-light-promoted three-component isocyanide-based synthesis of iminofurans is herein reported. The reaction proved to be general in scope and proceeds through a triple domino process. Control experiments with ¹⁸O-labeled water and TEMPO provided key mechanistic insights for delineating the reactivity paradigms crucial to design efficient photoredox isocyanide-based domino transformations.

Publication types

Research Support, Non-U.S. Gov't