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Redesign of a Pyrylium Photoredox Catalyst and Its Application to the Generation of Carbonyl Ylides

Edwin Alfonzo, Felix Steven Alfonso and Aaron B. Beeler*

*Department of Chemistry, Boston University, Boston, Massachusetts 02215, United States, Email: beelerabu.edu

E. Alfonzo, F. S. Alfonso, A. B. Beeler, Org. Lett., 2017, 19, 2989-2992.

DOI: 10.1021/acs.orglett.7b01222 (free Supporting Information)


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Abstract

4-Mesityl-2,6-diphenylpyrylium tetrafluoroborate (MDPT) and 4-mesityl-2,6-di-p-tolylpyrylium tetrafluoroborate (MD(p-tolyl)PT) are highly robust photoredox catalysts, and exhibit some of the highest oxidation potentials reported. Their utility was demonstrated in the mild and efficient generation of carbonyl ylides from benzylic epoxides.

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Key Words

2,5-dihydrofurans, photochemistry, organocatalysis


ID: J54-Y2017