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.gilmour
uni-muenster.de
J. B. Metternich, R. Gilmour, J. Am. Chem. Soc., 2016, 138, 1040-1045.
DOI: 10.1021/jacs.5b12081
see article for more reactions
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 E → Z isomerization step. The ensuing SET-based cyclization eliminates the need for a prefunctionalized aryl ring.
see article for more examples
Key Words
coumarins, oxygen, photochemistry
ID: J48-Y2016
