Photocatalytic Isocyanide-based Multicomponent Domino Cascade Towards 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 Towards the Stereoselective Formation of Iminofurans

Sveva Pelliccia
, Antonella Ilenia Alfano
, Paolo Luciano
, Ettore Novellino
, Alberto MASSAROTTI
, Gian Cesare TRON
, Davide Ravelli
, Mariateresa Giustiniano

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	1981-1990
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	85
Issue number	4
DOIs	https://doi.org/10.1021/acs.joc.9b02709
Publication status	Published - 2020

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10.1021/acs.joc.9b02709

http://hdl.handle.net/11579/107968

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title = "Photocatalytic Isocyanide-based Multicomponent Domino Cascade Towards the Stereoselective Formation of Iminofurans",

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.",

author = "Sveva Pelliccia and Alfano, \{Antonella Ilenia\} and Paolo Luciano and Ettore Novellino and Alberto MASSAROTTI and TRON, \{Gian Cesare\} and Davide Ravelli and Mariateresa Giustiniano",

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year = "2020",

doi = "10.1021/acs.joc.9b02709",

language = "English",

volume = "85",

pages = "1981--1990",

journal = "Journal of Organic Chemistry",

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T1 - Photocatalytic Isocyanide-based Multicomponent Domino Cascade Towards the Stereoselective Formation of Iminofurans

AU - Pelliccia, Sveva

AU - Alfano, Antonella Ilenia

AU - Luciano, Paolo

AU - Novellino, Ettore

AU - MASSAROTTI, Alberto

AU - TRON, Gian Cesare

AU - Ravelli, Davide

AU - Giustiniano, Mariateresa

PY - 2020

Y1 - 2020

N2 - 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.

AB - 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.

UR - https://iris.uniupo.it/handle/11579/107968

U2 - 10.1021/acs.joc.9b02709

DO - 10.1021/acs.joc.9b02709

M3 - Article

SN - 0022-3263

VL - 85

SP - 1981

EP - 1990

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 4

ER -

Photocatalytic Isocyanide-based Multicomponent Domino Cascade Towards the Stereoselective Formation of Iminofurans

Abstract

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