Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 39, Pages 11577-11580Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201503210
Keywords
fluorine; photocatalysis; radical reactions; ring expansion
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Funding
- NRW Graduate School of Chemistry
- Alexander von Humboldt Foundation
- Deutsche Forschungsgemeinschaft (Leibniz Award)
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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 alpha-(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.
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