Vitamin Catalysis: Direct, Photocatalytic Synthesis of Benzocoumarins via (−)-Riboflavin-Mediated Electron Transfer

An operationally simple protocol is disclosed to facilitate entry to benzo-3,4-coumarins directly from biaryl carboxylic acids without the need for substrate prefunctionalization. Complementary to classic lactonization strategies, this disconnection relies on the oxidation competence of photoactivat...

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Bibliographic Details
Published in:Organic letters 2018-03, Vol.20 (5), p.1316-1319
Main Authors: Morack, Tobias, Metternich, Jan B, Gilmour, Ryan
Format: Article
Language:English
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Summary:An operationally simple protocol is disclosed to facilitate entry to benzo-3,4-coumarins directly from biaryl carboxylic acids without the need for substrate prefunctionalization. Complementary to classic lactonization strategies, this disconnection relies on the oxidation competence of photoactivated (−)-riboflavin (vitamin B2) to generate the heterocyclic core via photoinduced single electron transfer. Collectively, the inexpensive nature of the catalyst, ease of execution, and absence of external metal additives are a convincing endorsement for the incorporation of simple vitamins in contemporary catalysis.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00052