Cargando…

Photocatalytic C−H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow

The functionalization of aryl C(sp(2))−H bonds is a useful strategy for the late‐stage modification of biologically active molecules, especially for the regioselective introduction of azole heterocycles to prepare medicinally‐relevant compounds. Herein, we describe a practical photocatalytic transfo...

Descripción completa

Detalles Bibliográficos
Autores principales: Wen, Zhenghui, Wan, Ting, Vijeta, Arjun, Casadevall, Carla, Buglioni, Laura, Reisner, Erwin, Noël, Timothy
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9298336/
https://www.ncbi.nlm.nih.gov/pubmed/34529334
http://dx.doi.org/10.1002/cssc.202101767
_version_ 1784750683784740864
author Wen, Zhenghui
Wan, Ting
Vijeta, Arjun
Casadevall, Carla
Buglioni, Laura
Reisner, Erwin
Noël, Timothy
author_facet Wen, Zhenghui
Wan, Ting
Vijeta, Arjun
Casadevall, Carla
Buglioni, Laura
Reisner, Erwin
Noël, Timothy
author_sort Wen, Zhenghui
collection PubMed
description The functionalization of aryl C(sp(2))−H bonds is a useful strategy for the late‐stage modification of biologically active molecules, especially for the regioselective introduction of azole heterocycles to prepare medicinally‐relevant compounds. Herein, we describe a practical photocatalytic transformation using a mesoporous carbon nitride (mpg‐CN( x )) photocatalyst, which enables the efficient azolation of various arenes through direct oxidation. The method exhibits a broad substrate scope and is amenable to the late‐stage functionalization of several pharmaceuticals. Due to the heterogeneous nature and high photocatalytic stability of mpg‐CN( x ), the catalyst can be easily recovered and reused leading to greener and more sustainable routes, using either batch or flow processing, to prepare these important compounds of interest in pharmaceutical and agrochemical research.
format Online
Article
Text
id pubmed-9298336
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-92983362022-07-21 Photocatalytic C−H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow Wen, Zhenghui Wan, Ting Vijeta, Arjun Casadevall, Carla Buglioni, Laura Reisner, Erwin Noël, Timothy ChemSusChem Full Papers The functionalization of aryl C(sp(2))−H bonds is a useful strategy for the late‐stage modification of biologically active molecules, especially for the regioselective introduction of azole heterocycles to prepare medicinally‐relevant compounds. Herein, we describe a practical photocatalytic transformation using a mesoporous carbon nitride (mpg‐CN( x )) photocatalyst, which enables the efficient azolation of various arenes through direct oxidation. The method exhibits a broad substrate scope and is amenable to the late‐stage functionalization of several pharmaceuticals. Due to the heterogeneous nature and high photocatalytic stability of mpg‐CN( x ), the catalyst can be easily recovered and reused leading to greener and more sustainable routes, using either batch or flow processing, to prepare these important compounds of interest in pharmaceutical and agrochemical research. John Wiley and Sons Inc. 2021-10-22 2021-12-06 /pmc/articles/PMC9298336/ /pubmed/34529334 http://dx.doi.org/10.1002/cssc.202101767 Text en © 2021 The Authors. ChemSusChem published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Wen, Zhenghui
Wan, Ting
Vijeta, Arjun
Casadevall, Carla
Buglioni, Laura
Reisner, Erwin
Noël, Timothy
Photocatalytic C−H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow
title Photocatalytic C−H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow
title_full Photocatalytic C−H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow
title_fullStr Photocatalytic C−H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow
title_full_unstemmed Photocatalytic C−H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow
title_short Photocatalytic C−H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow
title_sort photocatalytic c−h azolation of arenes using heterogeneous carbon nitride in batch and flow
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9298336/
https://www.ncbi.nlm.nih.gov/pubmed/34529334
http://dx.doi.org/10.1002/cssc.202101767
work_keys_str_mv AT wenzhenghui photocatalyticchazolationofarenesusingheterogeneouscarbonnitrideinbatchandflow
AT wanting photocatalyticchazolationofarenesusingheterogeneouscarbonnitrideinbatchandflow
AT vijetaarjun photocatalyticchazolationofarenesusingheterogeneouscarbonnitrideinbatchandflow
AT casadevallcarla photocatalyticchazolationofarenesusingheterogeneouscarbonnitrideinbatchandflow
AT buglionilaura photocatalyticchazolationofarenesusingheterogeneouscarbonnitrideinbatchandflow
AT reisnererwin photocatalyticchazolationofarenesusingheterogeneouscarbonnitrideinbatchandflow
AT noeltimothy photocatalyticchazolationofarenesusingheterogeneouscarbonnitrideinbatchandflow