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.
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