Metal-Free Multicatalytic Decarbonylation of Aldehydes Driven by Light

Augustin Nouaille; Francesco Terzani; Yara Fakih; Jérôme Hannedouche; Emmanuel Magnier; Corinne Gosmini; Guillaume Dagousset

doi:10.1002/anie.202424459

Metal-Free Multicatalytic Decarbonylation of Aldehydes Driven by Light

Augustin Nouaille, Francesco Terzani, Yara Fakih, Jérôme Hannedouche, Emmanuel Magnier, Corinne Gosmini, Guillaume Dagousset

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

Abstract

A metal-free dual photo- and organocatalytic decarbonylation of aliphatic aldehydes is described for the first time. On the one hand, a wide range of tertiary aldehydes are smoothly decarbonylated thanks to the combination of thioxanthone as photocatalyst and diphenyl disulfide as organocatalyst. On the other hand, by simply using 4-CzIPN as photocatalyst instead of thioxanthone, various secondary aldehydes readily undergo decarbonylation in an orthogonal manner, via the in situ formation of 1,4-dihydropyridines. Both methodologies are compatible with various functional groups and are readily applied to the decarbonylation of complex molecules.

Original language	English
Journal	Angewandte Chemie - International Edition
DOIs	https://doi.org/10.1002/anie.202424459
Publication status	Accepted/In press - 1 Jan 2025
Externally published	Yes

Keywords

aldehydes
decarbonylation
metal-free
organocatalysis
photocatalysis

Access to Document

10.1002/anie.202424459

Cite this

@article{d12a2fb65dc34bac9189923225cac9b1,

title = "Metal-Free Multicatalytic Decarbonylation of Aldehydes Driven by Light",

abstract = "A metal-free dual photo- and organocatalytic decarbonylation of aliphatic aldehydes is described for the first time. On the one hand, a wide range of tertiary aldehydes are smoothly decarbonylated thanks to the combination of thioxanthone as photocatalyst and diphenyl disulfide as organocatalyst. On the other hand, by simply using 4-CzIPN as photocatalyst instead of thioxanthone, various secondary aldehydes readily undergo decarbonylation in an orthogonal manner, via the in situ formation of 1,4-dihydropyridines. Both methodologies are compatible with various functional groups and are readily applied to the decarbonylation of complex molecules.",

keywords = "aldehydes, decarbonylation, metal-free, organocatalysis, photocatalysis",

author = "Augustin Nouaille and Francesco Terzani and Yara Fakih and J{\'e}r{\^o}me Hannedouche and Emmanuel Magnier and Corinne Gosmini and Guillaume Dagousset",

note = "Publisher Copyright: {\textcopyright} 2025 The Author(s). Angewandte Chemie International Edition published by Wiley-VCH GmbH.",

year = "2025",

month = jan,

day = "1",

doi = "10.1002/anie.202424459",

language = "English",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

}

TY - JOUR

T1 - Metal-Free Multicatalytic Decarbonylation of Aldehydes Driven by Light

AU - Nouaille, Augustin

AU - Terzani, Francesco

AU - Fakih, Yara

AU - Hannedouche, Jérôme

AU - Magnier, Emmanuel

AU - Gosmini, Corinne

AU - Dagousset, Guillaume

PY - 2025/1/1

Y1 - 2025/1/1

N2 - A metal-free dual photo- and organocatalytic decarbonylation of aliphatic aldehydes is described for the first time. On the one hand, a wide range of tertiary aldehydes are smoothly decarbonylated thanks to the combination of thioxanthone as photocatalyst and diphenyl disulfide as organocatalyst. On the other hand, by simply using 4-CzIPN as photocatalyst instead of thioxanthone, various secondary aldehydes readily undergo decarbonylation in an orthogonal manner, via the in situ formation of 1,4-dihydropyridines. Both methodologies are compatible with various functional groups and are readily applied to the decarbonylation of complex molecules.

AB - A metal-free dual photo- and organocatalytic decarbonylation of aliphatic aldehydes is described for the first time. On the one hand, a wide range of tertiary aldehydes are smoothly decarbonylated thanks to the combination of thioxanthone as photocatalyst and diphenyl disulfide as organocatalyst. On the other hand, by simply using 4-CzIPN as photocatalyst instead of thioxanthone, various secondary aldehydes readily undergo decarbonylation in an orthogonal manner, via the in situ formation of 1,4-dihydropyridines. Both methodologies are compatible with various functional groups and are readily applied to the decarbonylation of complex molecules.

KW - aldehydes

KW - decarbonylation

KW - metal-free

KW - organocatalysis

KW - photocatalysis

UR - https://www.scopus.com/pages/publications/85216870846

U2 - 10.1002/anie.202424459

DO - 10.1002/anie.202424459

M3 - Article

AN - SCOPUS:85216870846

SN - 1433-7851

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

ER -

Metal-Free Multicatalytic Decarbonylation of Aldehydes Driven by Light

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this