Combined Photoredox and Lewis Acid Catalyzed α-Hydroxyalkylation of Cyclic Ethers with Aromatic Ketones

Melissa Reckenthäler; Jörg-M Neudörfl; Elif Zorlu; Axel G Griesbeck

doi:10.1021/acs.joc.6b01085

Combined Photoredox and Lewis Acid Catalyzed α-Hydroxyalkylation of Cyclic Ethers with Aromatic Ketones

J Org Chem. 2016 Aug 19;81(16):7211-6. doi: 10.1021/acs.joc.6b01085. Epub 2016 Jul 20.

Authors

Melissa Reckenthäler¹, Jörg-M Neudörfl¹, Elif Zorlu¹, Axel G Griesbeck¹

Affiliation

¹ Department of Chemistry, University of Cologne , Greinstr. 4, Cologne D-50939, Germany.

PMID: 27380313
DOI: 10.1021/acs.joc.6b01085

Abstract

The photochemically induced coupling of aromatic ketones with cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane was studied. Direct photolysis of the substrates with UV-A light centered at 350 nm does not lead to photoinduced hydrogen transfer whereas the addition of a mixture of the Lewis acid catalysts Ti(O(i)Pr)4 and BF3 enables the formation of the hydroxyalkylation products.

Publication types

Research Support, Non-U.S. Gov't