Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media
- Autores
- Yerien, Damián Emilio; Groppi, Jessica; Postigo, Jose Alberto; Credi, Alberto; Conde, Romina Soledad; Baroncini, Massimo; Barata Vallejo, Sebastian
- Año de publicación
- 2023
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Modified crown ethers are fundamental building blocks in supramolecular chemistry, with applications in phase transfer catalysis, metal extraction, smart materials, and molecular machines. Here we report on a one-pot highly chemo- and regioselective photocatalytic fluoroalkylation protocol for the mono-functionalization of benzo substituted crown ethers. For this important class of macrocycles, the method described here represents one of the few late-stage functionalization procedures that is both high yielding and scalable. Because of its breadth of scope and substrate tolerance, the devised approach can be applied to a wide range of aromatic crown ethers (18 examples, up to 99 % yield), including those engaged in mechanically interlocked molecules.
Fil: Yerien, Damián Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consiglio Nazionale delle Ricerche; Italia
Fil: Groppi, Jessica. Consiglio Nazionale delle Ricerche; Italia
Fil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Credi, Alberto. Consiglio Nazionale delle Ricerche; Italia. Università di Bologna; Italia
Fil: Conde, Romina Soledad. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina
Fil: Baroncini, Massimo. Consiglio Nazionale delle Ricerche; Italia. Università di Bologna; Italia
Fil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina - Materia
-
CROWN COMPOUNDS
FLUOROALKYLATION
PHOTOCATALYSIS
ROTAXANES
WATER CHEMISTRY - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by/2.5/ar/
- Repositorio
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- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/225097
Ver los metadatos del registro completo
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Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous MediaYerien, Damián EmilioGroppi, JessicaPostigo, Jose AlbertoCredi, AlbertoConde, Romina SoledadBaroncini, MassimoBarata Vallejo, SebastianCROWN COMPOUNDSFLUOROALKYLATIONPHOTOCATALYSISROTAXANESWATER CHEMISTRYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Modified crown ethers are fundamental building blocks in supramolecular chemistry, with applications in phase transfer catalysis, metal extraction, smart materials, and molecular machines. Here we report on a one-pot highly chemo- and regioselective photocatalytic fluoroalkylation protocol for the mono-functionalization of benzo substituted crown ethers. For this important class of macrocycles, the method described here represents one of the few late-stage functionalization procedures that is both high yielding and scalable. Because of its breadth of scope and substrate tolerance, the devised approach can be applied to a wide range of aromatic crown ethers (18 examples, up to 99 % yield), including those engaged in mechanically interlocked molecules.Fil: Yerien, Damián Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consiglio Nazionale delle Ricerche; ItaliaFil: Groppi, Jessica. Consiglio Nazionale delle Ricerche; ItaliaFil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Credi, Alberto. Consiglio Nazionale delle Ricerche; Italia. Università di Bologna; ItaliaFil: Conde, Romina Soledad. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; ArgentinaFil: Baroncini, Massimo. Consiglio Nazionale delle Ricerche; Italia. Università di Bologna; ItaliaFil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; ArgentinaWiley VCH Verlag2023-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/225097Yerien, Damián Emilio; Groppi, Jessica; Postigo, Jose Alberto; Credi, Alberto; Conde, Romina Soledad; et al.; Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media; Wiley VCH Verlag; European Journal of Organic Chemistry; 26; 27; 7-2023; 1-91434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202300478info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.202300478info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:46:17Zoai:ri.conicet.gov.ar:11336/225097instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:46:18.186CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
| dc.title.none.fl_str_mv |
Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media |
| title |
Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media |
| spellingShingle |
Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media Yerien, Damián Emilio CROWN COMPOUNDS FLUOROALKYLATION PHOTOCATALYSIS ROTAXANES WATER CHEMISTRY |
| title_short |
Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media |
| title_full |
Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media |
| title_fullStr |
Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media |
| title_full_unstemmed |
Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media |
| title_sort |
Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media |
| dc.creator.none.fl_str_mv |
Yerien, Damián Emilio Groppi, Jessica Postigo, Jose Alberto Credi, Alberto Conde, Romina Soledad Baroncini, Massimo Barata Vallejo, Sebastian |
| author |
Yerien, Damián Emilio |
| author_facet |
Yerien, Damián Emilio Groppi, Jessica Postigo, Jose Alberto Credi, Alberto Conde, Romina Soledad Baroncini, Massimo Barata Vallejo, Sebastian |
| author_role |
author |
| author2 |
Groppi, Jessica Postigo, Jose Alberto Credi, Alberto Conde, Romina Soledad Baroncini, Massimo Barata Vallejo, Sebastian |
| author2_role |
author author author author author author |
| dc.subject.none.fl_str_mv |
CROWN COMPOUNDS FLUOROALKYLATION PHOTOCATALYSIS ROTAXANES WATER CHEMISTRY |
| topic |
CROWN COMPOUNDS FLUOROALKYLATION PHOTOCATALYSIS ROTAXANES WATER CHEMISTRY |
| purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| dc.description.none.fl_txt_mv |
Modified crown ethers are fundamental building blocks in supramolecular chemistry, with applications in phase transfer catalysis, metal extraction, smart materials, and molecular machines. Here we report on a one-pot highly chemo- and regioselective photocatalytic fluoroalkylation protocol for the mono-functionalization of benzo substituted crown ethers. For this important class of macrocycles, the method described here represents one of the few late-stage functionalization procedures that is both high yielding and scalable. Because of its breadth of scope and substrate tolerance, the devised approach can be applied to a wide range of aromatic crown ethers (18 examples, up to 99 % yield), including those engaged in mechanically interlocked molecules. Fil: Yerien, Damián Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consiglio Nazionale delle Ricerche; Italia Fil: Groppi, Jessica. Consiglio Nazionale delle Ricerche; Italia Fil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina Fil: Credi, Alberto. Consiglio Nazionale delle Ricerche; Italia. Università di Bologna; Italia Fil: Conde, Romina Soledad. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina Fil: Baroncini, Massimo. Consiglio Nazionale delle Ricerche; Italia. Università di Bologna; Italia Fil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina |
| description |
Modified crown ethers are fundamental building blocks in supramolecular chemistry, with applications in phase transfer catalysis, metal extraction, smart materials, and molecular machines. Here we report on a one-pot highly chemo- and regioselective photocatalytic fluoroalkylation protocol for the mono-functionalization of benzo substituted crown ethers. For this important class of macrocycles, the method described here represents one of the few late-stage functionalization procedures that is both high yielding and scalable. Because of its breadth of scope and substrate tolerance, the devised approach can be applied to a wide range of aromatic crown ethers (18 examples, up to 99 % yield), including those engaged in mechanically interlocked molecules. |
| publishDate |
2023 |
| dc.date.none.fl_str_mv |
2023-07 |
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info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
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article |
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publishedVersion |
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http://hdl.handle.net/11336/225097 Yerien, Damián Emilio; Groppi, Jessica; Postigo, Jose Alberto; Credi, Alberto; Conde, Romina Soledad; et al.; Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media; Wiley VCH Verlag; European Journal of Organic Chemistry; 26; 27; 7-2023; 1-9 1434-193X CONICET Digital CONICET |
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http://hdl.handle.net/11336/225097 |
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Yerien, Damián Emilio; Groppi, Jessica; Postigo, Jose Alberto; Credi, Alberto; Conde, Romina Soledad; et al.; Late-Stage Photocatalytic Fluoroalkylation of Aromatic Crown Ethers in Aqueous Media; Wiley VCH Verlag; European Journal of Organic Chemistry; 26; 27; 7-2023; 1-9 1434-193X CONICET Digital CONICET |
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eng |
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eng |
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Wiley VCH Verlag |
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Wiley VCH Verlag |
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CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
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dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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