Photocatalytic Dehydrogenative Lactonization of 2-Arylbenzoic Acids

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Title: Photocatalytic Dehydrogenative Lactonization of 2-Arylbenzoic Acids
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).
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
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Appears in Collections:INV - CESO - Artículos de Revistas
INV - SINTAS - Artículos de Revistas

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