Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes

A light-driven metal-free protocol for the synthesis of sulfone-containing indoles under mild conditions is reported. Specifically, the process is driven by the photochemical activity of halogen-bonded complexes formed upon complexation of a sacrificial donor, namely 1,4-diazabicyclo[2.2.2]octane (D...

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Autores principales: Mamone, Martina, Gentile, Giuseppe, Dosso, Jacopo, Prato, Maurizio, Filippini, Giacomo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10155616/
https://www.ncbi.nlm.nih.gov/pubmed/37153645
http://dx.doi.org/10.3762/bjoc.19.42
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author Mamone, Martina
Gentile, Giuseppe
Dosso, Jacopo
Prato, Maurizio
Filippini, Giacomo
author_facet Mamone, Martina
Gentile, Giuseppe
Dosso, Jacopo
Prato, Maurizio
Filippini, Giacomo
author_sort Mamone, Martina
collection PubMed
description A light-driven metal-free protocol for the synthesis of sulfone-containing indoles under mild conditions is reported. Specifically, the process is driven by the photochemical activity of halogen-bonded complexes formed upon complexation of a sacrificial donor, namely 1,4-diazabicyclo[2.2.2]octane (DABCO), with α-iodosulfones. The reaction provides a variety of densely functionalized products in good yields (up to 96% yield). Mechanistic investigations are reported. These studies provide convincing evidences for the photochemical formation of reactive open-shell species.
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spelling pubmed-101556162023-05-04 Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes Mamone, Martina Gentile, Giuseppe Dosso, Jacopo Prato, Maurizio Filippini, Giacomo Beilstein J Org Chem Letter A light-driven metal-free protocol for the synthesis of sulfone-containing indoles under mild conditions is reported. Specifically, the process is driven by the photochemical activity of halogen-bonded complexes formed upon complexation of a sacrificial donor, namely 1,4-diazabicyclo[2.2.2]octane (DABCO), with α-iodosulfones. The reaction provides a variety of densely functionalized products in good yields (up to 96% yield). Mechanistic investigations are reported. These studies provide convincing evidences for the photochemical formation of reactive open-shell species. Beilstein-Institut 2023-04-27 /pmc/articles/PMC10155616/ /pubmed/37153645 http://dx.doi.org/10.3762/bjoc.19.42 Text en Copyright © 2023, Mamone et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Letter
Mamone, Martina
Gentile, Giuseppe
Dosso, Jacopo
Prato, Maurizio
Filippini, Giacomo
Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes
title Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes
title_full Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes
title_fullStr Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes
title_full_unstemmed Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes
title_short Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes
title_sort direct c2–h alkylation of indoles driven by the photochemical activity of halogen-bonded complexes
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10155616/
https://www.ncbi.nlm.nih.gov/pubmed/37153645
http://dx.doi.org/10.3762/bjoc.19.42
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