Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers

Franck Le Vaillant; Marion Garreau; Stefano Nicolai; Ganna Gryn'ova; Clemence Corminboeuf; Jerome Waser

doi:10.1039/C8SC01818A

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Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers†

Franck Le Vaillant,

^a Marion Garreau,

^a Stefano Nicolai,

^a Ganna Gryn'ova,

^b Clemence Corminboeuf

^b and Jerome Waser

*^a

Author affiliations

* Corresponding authors

^a Laboratory of Catalysis and Organic Synthesis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, Ch-1015, Lausanne, Switzerland
E-mail: jerome.waser@epfl.ch

^b Laboratory for Computational Molecular Design, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, Ch-1015, Lausanne, Switzerland

Abstract

Fine-tuned organic photoredox catalysts are introduced for the metal-free alkynylation of alkylnitrile radicals generated via oxidative ring opening of cyclic alkylketone oxime ethers. The redox properties of the dyes were determined by both cyclic voltammetry and computation and covered an existing gap in the oxidation potential of photoredox organocatalysts.

This article is part of the themed collections: Most popular 2018-2019 catalysis articles, Editor's choice - Paolo Melchiorre, Functional Organic Materials Symposium Collection and 2018 Chemical Science HOT Article Collection

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DOI: https://doi.org/10.1039/C8SC01818A
Article type: Edge Article
Submitted: 20 Apr 2018
Accepted: 28 May 2018
First published: 30 May 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2018,9, 5883-5889

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Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers

F. Le Vaillant, M. Garreau, S. Nicolai, G. Gryn'ova, C. Corminboeuf and J. Waser, Chem. Sci., 2018, 9, 5883 DOI: 10.1039/C8SC01818A

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Chemical Science

Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers†

Abstract

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Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers

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