title: Visible-Light-Mediated Achmatowicz Rearrangement.
abstract: Visible-light-mediated photoredox catalysis is a viable method to access highly reactive intermediates from cheap, readily available, and shelf-stable reagents to perform clean chemical transformations. Here, we report the first photoredox-catalyzed Achmatowicz reaction of furfuryl alcohol derivatives to produce functionalized dihydropyranones while only forming easily separable NaHSO4as a byproduct. The water solubility of the byproduct facilitates direct Boc-protection of the resulting hemiacetal without the need for column purification. The reaction is very robust and permits the use of various aqueous solutions and light sources including sunlight.
authors.affiliation: Department of Biomolecular Systems, Max-Planck Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.
authors.forename: Matthew B
authors.initials: MB
authors.lastname: Plutschack
authors.affiliation: Department of Biomolecular Systems, Max-Planck Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.|Institute of Chemistry and Biochemistry, Department of Biology, Chemistry and Pharmacy, Freie Universität Berlin , Arnimallee 22, 14195 Berlin, Germany.
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
authors.affiliation: Department of Biomolecular Systems, Max-Planck Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.
authors.forename: Kerry
authors.identifier: 0000-0001-9897-6017
authors.initials: K
authors.lastname: Gilmore