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Photoredox Cross-Dehydrogenative Coupling of N-Aryl Glycines Mediated by Mesoporous Graphitic Carbon Nitride: An Environmentally Friendly Approach to the Synthesis of Non-Proteinogenic α-Amino Acids (NPAAs) Decorated with Indoles
[Image: see text] Indole-decorated glycine derivatives are prepared through an environmentally benign cross-dehydrogenative coupling between N-aryl glycine analogues and indoles (yield of ≤81%). Merging heterogeneous organocatalysis and photocatalysis, C–H functionalization has been achieved by sele...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9207928/ https://www.ncbi.nlm.nih.gov/pubmed/35621232 http://dx.doi.org/10.1021/acs.joc.2c00474 |
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author | Poletti, Lorenzo Ragno, Daniele Bortolini, Olga Presini, Francesco Pesciaioli, Fabio Carli, Stefano Caramori, Stefano Molinari, Alessandra Massi, Alessandro Di Carmine, Graziano |
author_facet | Poletti, Lorenzo Ragno, Daniele Bortolini, Olga Presini, Francesco Pesciaioli, Fabio Carli, Stefano Caramori, Stefano Molinari, Alessandra Massi, Alessandro Di Carmine, Graziano |
author_sort | Poletti, Lorenzo |
collection | PubMed |
description | [Image: see text] Indole-decorated glycine derivatives are prepared through an environmentally benign cross-dehydrogenative coupling between N-aryl glycine analogues and indoles (yield of ≤81%). Merging heterogeneous organocatalysis and photocatalysis, C–H functionalization has been achieved by selective C-2 oxidation of N-aryl glycines to afford the electrophilic imine followed by Friedel–Crafts alkylation with indole. The sustainability of the process has been taken into account in the reaction design through the implementation of a metal-free recyclable heterogeneous photocatalyst and a green reaction medium. Scale-up of the benchmark reaction (gram scale, yield of 69%) and recycling experiments (over seven runs without a loss of efficiency) have been performed to prove the robustness of the protocol. Finally, mechanistic studies were conducted employing electron paramagnetic resonance spectroscopy to unveil the roles of the photocatalyst and oxygen in the formation of odd-electron species. |
format | Online Article Text |
id | pubmed-9207928 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-92079282022-06-21 Photoredox Cross-Dehydrogenative Coupling of N-Aryl Glycines Mediated by Mesoporous Graphitic Carbon Nitride: An Environmentally Friendly Approach to the Synthesis of Non-Proteinogenic α-Amino Acids (NPAAs) Decorated with Indoles Poletti, Lorenzo Ragno, Daniele Bortolini, Olga Presini, Francesco Pesciaioli, Fabio Carli, Stefano Caramori, Stefano Molinari, Alessandra Massi, Alessandro Di Carmine, Graziano J Org Chem [Image: see text] Indole-decorated glycine derivatives are prepared through an environmentally benign cross-dehydrogenative coupling between N-aryl glycine analogues and indoles (yield of ≤81%). Merging heterogeneous organocatalysis and photocatalysis, C–H functionalization has been achieved by selective C-2 oxidation of N-aryl glycines to afford the electrophilic imine followed by Friedel–Crafts alkylation with indole. The sustainability of the process has been taken into account in the reaction design through the implementation of a metal-free recyclable heterogeneous photocatalyst and a green reaction medium. Scale-up of the benchmark reaction (gram scale, yield of 69%) and recycling experiments (over seven runs without a loss of efficiency) have been performed to prove the robustness of the protocol. Finally, mechanistic studies were conducted employing electron paramagnetic resonance spectroscopy to unveil the roles of the photocatalyst and oxygen in the formation of odd-electron species. American Chemical Society 2022-05-27 2022-06-17 /pmc/articles/PMC9207928/ /pubmed/35621232 http://dx.doi.org/10.1021/acs.joc.2c00474 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 | Poletti, Lorenzo Ragno, Daniele Bortolini, Olga Presini, Francesco Pesciaioli, Fabio Carli, Stefano Caramori, Stefano Molinari, Alessandra Massi, Alessandro Di Carmine, Graziano Photoredox Cross-Dehydrogenative Coupling of N-Aryl Glycines Mediated by Mesoporous Graphitic Carbon Nitride: An Environmentally Friendly Approach to the Synthesis of Non-Proteinogenic α-Amino Acids (NPAAs) Decorated with Indoles |
title | Photoredox Cross-Dehydrogenative
Coupling of N-Aryl Glycines Mediated by Mesoporous
Graphitic
Carbon Nitride: An Environmentally Friendly Approach to the Synthesis
of Non-Proteinogenic α-Amino Acids (NPAAs) Decorated
with Indoles |
title_full | Photoredox Cross-Dehydrogenative
Coupling of N-Aryl Glycines Mediated by Mesoporous
Graphitic
Carbon Nitride: An Environmentally Friendly Approach to the Synthesis
of Non-Proteinogenic α-Amino Acids (NPAAs) Decorated
with Indoles |
title_fullStr | Photoredox Cross-Dehydrogenative
Coupling of N-Aryl Glycines Mediated by Mesoporous
Graphitic
Carbon Nitride: An Environmentally Friendly Approach to the Synthesis
of Non-Proteinogenic α-Amino Acids (NPAAs) Decorated
with Indoles |
title_full_unstemmed | Photoredox Cross-Dehydrogenative
Coupling of N-Aryl Glycines Mediated by Mesoporous
Graphitic
Carbon Nitride: An Environmentally Friendly Approach to the Synthesis
of Non-Proteinogenic α-Amino Acids (NPAAs) Decorated
with Indoles |
title_short | Photoredox Cross-Dehydrogenative
Coupling of N-Aryl Glycines Mediated by Mesoporous
Graphitic
Carbon Nitride: An Environmentally Friendly Approach to the Synthesis
of Non-Proteinogenic α-Amino Acids (NPAAs) Decorated
with Indoles |
title_sort | photoredox cross-dehydrogenative
coupling of n-aryl glycines mediated by mesoporous
graphitic
carbon nitride: an environmentally friendly approach to the synthesis
of non-proteinogenic α-amino acids (npaas) decorated
with indoles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9207928/ https://www.ncbi.nlm.nih.gov/pubmed/35621232 http://dx.doi.org/10.1021/acs.joc.2c00474 |
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