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- Title
Visible-Light Photoredox-Catalyzed Semipinacol-Type Rearrangement: Trifluoromethylation/Ring Expansion by a Radical-Polar Mechanism.
- Authors
Sahoo, Basudev; Li, Jun-Long; Glorius, Frank
- Abstract
A visible-light-mediated photoredox-catalyzed semipinacol-type rearrangement proceeding via 1,2 alkyl migration was developed. In this transformation, trifluoromethylation of the CC 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.
- Subjects
PHOTOCATALYSIS; LIGHT absorption; PINACOL rearrangement; CARBON-carbon bonds; STYRENE derivatives
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 39, p11577
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201503210