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Difluoroalkylation of Anilines via Photoinduced Methods

[Image: see text] The development of sustainable and mild protocols for the fluoroalkylation of organic backbones is of current interest in chemical organic synthesis. Herein, we present operationally simple and practical transition-metal-free methods for the preparation of difluoroalkyl anilines. F...

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Autores principales: Gallego-Gamo, Albert, Granados, Albert, Pleixats, Roser, Gimbert-Suriñach, Carolina, Vallribera, Adelina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476199/
https://www.ncbi.nlm.nih.gov/pubmed/37585266
http://dx.doi.org/10.1021/acs.joc.3c01298
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author Gallego-Gamo, Albert
Granados, Albert
Pleixats, Roser
Gimbert-Suriñach, Carolina
Vallribera, Adelina
author_facet Gallego-Gamo, Albert
Granados, Albert
Pleixats, Roser
Gimbert-Suriñach, Carolina
Vallribera, Adelina
author_sort Gallego-Gamo, Albert
collection PubMed
description [Image: see text] The development of sustainable and mild protocols for the fluoroalkylation of organic backbones is of current interest in chemical organic synthesis. Herein, we present operationally simple and practical transition-metal-free methods for the preparation of difluoroalkyl anilines. First, a visible-light organophotocatalytic system working via oxidative quenching is described, providing access to a wide range of difluoroalkyl anilines under mild conditions. In addition, the formation of an unprecedented electron donor–acceptor (EDA) complex between anilines and ethyl difluoroiodoacetate is reported and exploited as an alternative, efficient, and straightforward strategy to prepare difluoroalkyl derivatives.
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spelling pubmed-104761992023-09-05 Difluoroalkylation of Anilines via Photoinduced Methods Gallego-Gamo, Albert Granados, Albert Pleixats, Roser Gimbert-Suriñach, Carolina Vallribera, Adelina J Org Chem [Image: see text] The development of sustainable and mild protocols for the fluoroalkylation of organic backbones is of current interest in chemical organic synthesis. Herein, we present operationally simple and practical transition-metal-free methods for the preparation of difluoroalkyl anilines. First, a visible-light organophotocatalytic system working via oxidative quenching is described, providing access to a wide range of difluoroalkyl anilines under mild conditions. In addition, the formation of an unprecedented electron donor–acceptor (EDA) complex between anilines and ethyl difluoroiodoacetate is reported and exploited as an alternative, efficient, and straightforward strategy to prepare difluoroalkyl derivatives. American Chemical Society 2023-08-16 /pmc/articles/PMC10476199/ /pubmed/37585266 http://dx.doi.org/10.1021/acs.joc.3c01298 Text en © 2023 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 Gallego-Gamo, Albert
Granados, Albert
Pleixats, Roser
Gimbert-Suriñach, Carolina
Vallribera, Adelina
Difluoroalkylation of Anilines via Photoinduced Methods
title Difluoroalkylation of Anilines via Photoinduced Methods
title_full Difluoroalkylation of Anilines via Photoinduced Methods
title_fullStr Difluoroalkylation of Anilines via Photoinduced Methods
title_full_unstemmed Difluoroalkylation of Anilines via Photoinduced Methods
title_short Difluoroalkylation of Anilines via Photoinduced Methods
title_sort difluoroalkylation of anilines via photoinduced methods
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476199/
https://www.ncbi.nlm.nih.gov/pubmed/37585266
http://dx.doi.org/10.1021/acs.joc.3c01298
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