Organic Letters
Organic Letters
5 years ago

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

Vitamin Catalysis: Direct, Photocatalytic Synthesis of Benzocoumarins via (−)-Riboflavin-Mediated Electron Transfer
Jan B. Metternich, Ryan Gilmour, Tobias Morack
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.8b00052

DOI: 10.1021/acs.orglett.8b00052

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