A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides

[Image: see text] Indoles are among the most important N-heterocycles in pharmaceuticals. Here, we present an alternative to the classic Fischer indole synthesis based on the radical coupling between aryl diazoniums and alkyl iodides. This iron-mediated strategy features a double role for the aryl d...

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Autores principales: Govaerts, Sebastian, Nakamura, Kento, Constantin, Timothée, Leonori, Daniele
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9641658/
https://www.ncbi.nlm.nih.gov/pubmed/36268790
http://dx.doi.org/10.1021/acs.orglett.2c02840
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author Govaerts, Sebastian
Nakamura, Kento
Constantin, Timothée
Leonori, Daniele
author_facet Govaerts, Sebastian
Nakamura, Kento
Constantin, Timothée
Leonori, Daniele
author_sort Govaerts, Sebastian
collection PubMed
description [Image: see text] Indoles are among the most important N-heterocycles in pharmaceuticals. Here, we present an alternative to the classic Fischer indole synthesis based on the radical coupling between aryl diazoniums and alkyl iodides. This iron-mediated strategy features a double role for the aryl diazoniums that sequentially activate the alkyl iodides through halogen-atom transfer and then serve as radical acceptors. The process operates under mild conditions and enables the preparation of densely functionalized indoles.
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spelling pubmed-96416582022-11-15 A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides Govaerts, Sebastian Nakamura, Kento Constantin, Timothée Leonori, Daniele Org Lett [Image: see text] Indoles are among the most important N-heterocycles in pharmaceuticals. Here, we present an alternative to the classic Fischer indole synthesis based on the radical coupling between aryl diazoniums and alkyl iodides. This iron-mediated strategy features a double role for the aryl diazoniums that sequentially activate the alkyl iodides through halogen-atom transfer and then serve as radical acceptors. The process operates under mild conditions and enables the preparation of densely functionalized indoles. American Chemical Society 2022-10-21 2022-11-04 /pmc/articles/PMC9641658/ /pubmed/36268790 http://dx.doi.org/10.1021/acs.orglett.2c02840 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Govaerts, Sebastian
Nakamura, Kento
Constantin, Timothée
Leonori, Daniele
A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides
title A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides
title_full A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides
title_fullStr A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides
title_full_unstemmed A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides
title_short A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides
title_sort halogen-atom transfer (xat)-based approach to indole synthesis using aryl diazonium salts and alkyl iodides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9641658/
https://www.ncbi.nlm.nih.gov/pubmed/36268790
http://dx.doi.org/10.1021/acs.orglett.2c02840
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