Journal
ORGANIC LETTERS
Volume 17, Issue 18, Pages 4550-4553Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02269
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- Spanish Ministerio de Ciencia e Innovacion [CTQ2011-24165]
- Generalitat Valenciana [ACIF/2011/159]
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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)(2)S2O8 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.
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