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One Photocatalyst, n Activation Modes Strategy for Cascade Catalysis: Emulating Coumarin Biosynthesis with (-)-Riboflavin

Jan B. Metternich and Ryan Gilmour*

*Institute for Organic Chemistry, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany, Email: ryan.gilmouruni-muenster.de

J. B. Metternich, R. Gilmour, J. Am. Chem. Soc., 2016, 138, 1040-1045.

DOI: 10.1021/jacs.5b12081 (free Supporting Information)


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Abstract

The two discrete photochemical activation modes of (-)-riboflavin sequentially induce isomerization and cyclization by energy transfer (ET) and single-electron transfer (SET) activation pathways in an emulation of the coumarin biosynthesis pathway via a key photochemical EZ isomerization step. The ensuing SET-based cyclization eliminates the need for a prefunctionalized aryl ring.

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Key Words

coumarins, oxygen, photochemistry


ID: J48-Y2016