Trityl isocyanide as a general reagent for visible light mediated photoredox-catalyzed cyanations

A photoredox catalytic strategy has been developed to enable the functionalization of a variety of commercially available, structurally different radical precursors by the use of a bench-stable isonitrile as an efficient cyanating reagent. Specifically, a radical-based reaction has provided a mild a...

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Detalhes bibliográficos
Autores: Quirós Pérez, Irene, Martín Martín, María, Pérez Sánchez, Carla, Rigotti, Thomas, Tortosa Manzanares, Mariola
Formato: artículo
Fecha de publicación:2024
País:España
Recursos:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/715517
Acesso em linha:http://hdl.handle.net/10486/715517
https://dx.doi.org/10.1039/d4sc04199b
Access Level:acceso abierto
Palavra-chave:Cyanation
Isocyanides
Isonitriles
Primary Radicals
Radical Precursor
Tertiary Radicals
Visible-Light Irradiation
Química
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spelling Trityl isocyanide as a general reagent for visible light mediated photoredox-catalyzed cyanationsQuirós Pérez, IreneMartín Martín, MaríaPérez Sánchez, CarlaRigotti, ThomasTortosa Manzanares, MariolaCyanationIsocyanidesIsonitrilesPrimary RadicalsRadical PrecursorTertiary RadicalsVisible-Light IrradiationQuímicaA photoredox catalytic strategy has been developed to enable the functionalization of a variety of commercially available, structurally different radical precursors by the use of a bench-stable isonitrile as an efficient cyanating reagent. Specifically, a radical-based reaction has provided a mild and convenient procedure for the cyanation of primary, secondary and tertiary radicals derived from widely accessible sp3-hybridized carboxylic acids, alcohols and halides under visible light irradiation. The reaction tolerates a variety of functional groups and it represents a complementary method for the cyanation of structurally different scaffolds that show diverse native functionalities, expanding the scope of previously reported methodologiesWe thank the European Research Council (ERC Consolidator Grant–101002715–SCAN) and the Spanish Ministry of Science and Innovation (MICINN) [PID2022-142594NB-I00] for financial support. M. M. and C. P.-S. acknowledge Ministerio de Universidades and MICINN for FPU (FPU20/06320) and for FPI (PREP2022-000243) fellowships, respectivelyRoyal Society of ChemistryDepartamento de Química OrgánicaFacultad de Ciencias20242024-08-06research articlehttp://purl.org/coar/resource_type/c_2df8fbb1VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10486/715517https://dx.doi.org/10.1039/d4sc04199breponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial 4.0 Internationalhttp://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/7155172026-06-23T12:46:27Z
dc.title.none.fl_str_mv Trityl isocyanide as a general reagent for visible light mediated photoredox-catalyzed cyanations
title Trityl isocyanide as a general reagent for visible light mediated photoredox-catalyzed cyanations
spellingShingle Trityl isocyanide as a general reagent for visible light mediated photoredox-catalyzed cyanations
Quirós Pérez, Irene
Cyanation
Isocyanides
Isonitriles
Primary Radicals
Radical Precursor
Tertiary Radicals
Visible-Light Irradiation
Química
title_short Trityl isocyanide as a general reagent for visible light mediated photoredox-catalyzed cyanations
title_full Trityl isocyanide as a general reagent for visible light mediated photoredox-catalyzed cyanations
title_fullStr Trityl isocyanide as a general reagent for visible light mediated photoredox-catalyzed cyanations
title_full_unstemmed Trityl isocyanide as a general reagent for visible light mediated photoredox-catalyzed cyanations
title_sort Trityl isocyanide as a general reagent for visible light mediated photoredox-catalyzed cyanations
dc.creator.none.fl_str_mv Quirós Pérez, Irene
Martín Martín, María
Pérez Sánchez, Carla
Rigotti, Thomas
Tortosa Manzanares, Mariola
author Quirós Pérez, Irene
author_facet Quirós Pérez, Irene
Martín Martín, María
Pérez Sánchez, Carla
Rigotti, Thomas
Tortosa Manzanares, Mariola
author_role author
author2 Martín Martín, María
Pérez Sánchez, Carla
Rigotti, Thomas
Tortosa Manzanares, Mariola
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Química Orgánica
Facultad de Ciencias
dc.subject.none.fl_str_mv Cyanation
Isocyanides
Isonitriles
Primary Radicals
Radical Precursor
Tertiary Radicals
Visible-Light Irradiation
Química
topic Cyanation
Isocyanides
Isonitriles
Primary Radicals
Radical Precursor
Tertiary Radicals
Visible-Light Irradiation
Química
description A photoredox catalytic strategy has been developed to enable the functionalization of a variety of commercially available, structurally different radical precursors by the use of a bench-stable isonitrile as an efficient cyanating reagent. Specifically, a radical-based reaction has provided a mild and convenient procedure for the cyanation of primary, secondary and tertiary radicals derived from widely accessible sp3-hybridized carboxylic acids, alcohols and halides under visible light irradiation. The reaction tolerates a variety of functional groups and it represents a complementary method for the cyanation of structurally different scaffolds that show diverse native functionalities, expanding the scope of previously reported methodologies
publishDate 2024
dc.date.none.fl_str_mv 2024
2024-08-06
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10486/715517
https://dx.doi.org/10.1039/d4sc04199b
url http://hdl.handle.net/10486/715517
https://dx.doi.org/10.1039/d4sc04199b
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial 4.0 International
http://creativecommons.org/licenses/by-nc/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial 4.0 International
http://creativecommons.org/licenses/by-nc/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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