Direct Decarboxylative Allylation and Arylation of Aliphatic Carboxylic Acids Using Flavin‐Mediated Photoredox Catalysis
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http://hdl.handle.net/10045/103987
Títol: | Direct Decarboxylative Allylation and Arylation of Aliphatic Carboxylic Acids Using Flavin‐Mediated Photoredox Catalysis |
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Autors: | Ramírez, Nieves P. | Lana-Villarreal, Teresa | Gonzalez-Gomez, Jose C. |
Grups d'investigació o GITE: | Nuevos Materiales y Catalizadores (MATCAT) | Grupo de Fotoquímica y Electroquímica de Semiconductores (GFES) |
Centre, Departament o Servei: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica | Universidad de Alicante. Departamento de Química Física | Universidad de Alicante. Instituto Universitario de Electroquímica |
Paraules clau: | Allylation | Carboxylic acids | Photocatalysis | Radicals | Sustainable chemistry |
Àrees de coneixement: | Química Orgánica | Química Física |
Data de publicació: | 15-de març-2020 |
Editor: | Wiley-VCH Verlag GmbH & Co. KGaA |
Citació bibliogràfica: | European Journal of Organic Chemistry. 2020, 10: 1539-1550. doi:10.1002/ejoc.201900888 |
Resum: | We describe herein a direct decarboxylative allylation of aliphatic carboxylic acids with allylsulfones using visible light and riboflavin tetraacetate (RFTA) as photocatalyst. The reaction proceeds at room temperature tolerating a wide range of functionalities, avoiding the use of external bases or additives. Mechanistic studies support that alkyl radicals are involved in the reaction and that a true photocatalytic cycle is operating. It is proposed that the carboxylic acid is deprotonated by [RFTA]·–, and the corresponding carboxylate acts as a reductive quencher of RFTA*, which after decarboxylation produces the alkyl radical. The methodology was adapted to prepare benzothiazoles substituted at C2, by reacting some carboxylic acids with 2‐(phenylsulfonyl)benzothiazole. The number of carboxylic acids suitable for this arylation was lower than for the allylation and this different reactivity was briefly commented. |
Patrocinadors: | This work was generously supported by the Spanish Ministerio de Economía y Competitividad (CTQ2017–88171-P) and the Generalitat Valenciana (AICO/2017/007). N. P. R. thanks to Instituto de Síntesis Orgánica for financial support. |
URI: | http://hdl.handle.net/10045/103987 |
ISSN: | 1434-193X (Print) | 1099-0690 (Online) |
DOI: | 10.1002/ejoc.201900888 |
Idioma: | eng |
Tipus: | info:eu-repo/semantics/article |
Drets: | © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
Revisió científica: | si |
Versió de l'editor: | https://doi.org/10.1002/ejoc.201900888 |
Apareix a la col·lecció: | INV - MATCAT - Artículos de Revistas INV - GFES - Artículos de Revistas |
Arxius per aquest ítem:
Arxiu | Descripció | Tamany | Format | |
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2020_Ramirez_etal_EurJOC_final.pdf | Versión final (acceso restringido) | 2,08 MB | Adobe PDF | Obrir Sol·licitar una còpia |
2020_Ramirez_etal_EurJOC_accepted.pdf | Accepted Manuscript (acceso abierto) | 2,52 MB | Adobe PDF | Obrir Vista prèvia |
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