Photocatalytic Dehydrogenative Lactonization of 2-Arylbenzoic Acids
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Title: | Photocatalytic Dehydrogenative Lactonization of 2-Arylbenzoic Acids |
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Authors: | Ramírez, Nieves P. | Bosque, Irene | Gonzalez-Gomez, Jose C. |
Research Group/s: | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Síntesis Asimétrica (SINTAS) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Keywords: | Photocatalytic | Dehydrogenative | Lactonization | 2-arylbenzoic acids |
Knowledge Area: | Química Orgánica |
Issue Date: | 31-Aug-2015 |
Publisher: | American Chemical Society |
Citation: | Organic Letters. 2015, 17(18): 4550-4553. doi:10.1021/acs.orglett.5b02269 |
Abstract: | A metal-free dehydrogenative lactonization of 2-arylbenzoic acids at room temperature was developed. This work illustrates the first application of visible-light photoredox catalysis in the preparation of benzo-3,4-coumarins, an important structural motif in bioactive molecules. The combination of photocatalyst [Acr+-Mes] with (NH4)2S2O8 as a terminal oxidant provides an economical and environmentally benign entry to different substituted benzocoumarins. Preliminary mechanistic studies suggest that this reaction most likely occurs through a homolytic aromatic substitution pathway. |
Sponsor: | We thank the Spanish Ministerio de Ciencia e Innovación (CTQ2011-24165) for financial support. I.B. acknowledges the Generalitat Valenciana for a postdoctoral fellowship (ACIF/2011/159). |
URI: | http://hdl.handle.net/10045/52884 |
ISSN: | 1523-7060 (Print) | 1523-7052 (Online) |
DOI: | 10.1021/acs.orglett.5b02269 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © 2015 American Chemical Society |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1021/acs.orglett.5b02269 |
Appears in Collections: | INV - CESO - Artículos de Revistas INV - SINTAS - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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2015_Ramirez_etal_OrgLett_final.pdf | Versión final (acceso restringido) | 770,52 kB | Adobe PDF | Open Request a copy |
2015_Ramirez_etal_OrgLett_rev.pdf | Versión revisada (acceso abierto) | 486,42 kB | Adobe PDF | Open Preview |
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