Tri(9-anthryl)borane was successfully
applied as an organophotocatalyst
for the visible-light-induced trifluoromethylation of unactivated
alkenes with CF3I. The mild reaction conditions tolerated
a variety of functional groups, and the reaction could be extended
to perfluoroalkylations with C3F7I and C4F9I. Mechanistic studies revealed that the photoredox
catalysis involves an oxidative quenching pathway.
Subtle differences in reaction conditions facilitated unprecedented photocatalytic reactions of oxadiazolines by energy transfer catalysis. A set of compounds, sulfoximines and benzimidazoles, were ingeniously prepared from oxadiazolines via nitrene intermediates by photocatalytic N−O/C−N bond cleavages. The synthesis of sulfoximines was realized through intermolecular N−S bond formation between nitrene intermediates and sulfoxides, whereas benzimidazoles were obtained via intramolecular aromatic substitution of the nitrene to the tethered aryl substituent.
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