title: Visible-Light Photoredox-Catalyzed Semipinacol-Type Rearrangement: Trifluoromethylation/Ring Expansion by a Radical-Polar Mechanism.
abstract: A visible-light-mediated photoredox-catalyzed semipinacol-type rearrangement proceeding via 1,2 alkyl migration was developed. In this transformation, trifluoromethylation of the C=C bond of α-(1-hydroxycycloalkyl)-substituted styrene derivatives is followed by ring expansion of the 1-hydroxycycloalkyl group to deliver novel cycloalkanones with all-carbon quaternary centers. The reaction proceeds via a radical-polar mechanism, with trifluoromethylation (radical) and ring expansion (ionic) occurring in the same transformation.
authors.affiliation: Westfälische Wilhelms-Universität Münster, International Graduate School of Chemistry & Organisch-Chemisches Institut, Corrensstrasse 40, 48149 Münster (Germany) http://www.uni-muenster.de/Chemie.oc/glorius/
authors.forename: Basudev
authors.initials: B
authors.lastname: Sahoo
authors.affiliation: Westfälische Wilhelms-Universität Münster, International Graduate School of Chemistry & Organisch-Chemisches Institut, Corrensstrasse 40, 48149 Münster (Germany) http://www.uni-muenster.de/Chemie.oc/glorius/
authors.forename: Jun-Long
authors.initials: JL
authors.lastname: Li
authors.affiliation: Westfälische Wilhelms-Universität Münster, International Graduate School of Chemistry & Organisch-Chemisches Institut, Corrensstrasse 40, 48149 Münster (Germany) http://www.uni-muenster.de/Chemie.oc/glorius/. glorius@uni-muenster.de.
authors.forename: Frank
authors.initials: F
authors.lastname: Glorius
keywords: fluorine; photocatalysis; radical reactions; ring expansion