2 research outputs found
α‑<i>N</i>‑Heteroarylation and α‑Azidation of Ketones via Enolonium Species
Enolonium species, resulting from
the umpolung of ketone enolates
by Koser’s hypervalent iodine reagents activated by boron trifluoride,
react with a variety of nitrogen heterocycles to form α-aminated
ketones. The reactions are mild and complete in 4–5 h. Additionally,
α-azidation of the enolonium species takes place using trimethylsilyl
azide as a convenient source of azide nucleophile
Transition-Metal-Free Intermolecular α‑Arylation of Ketones via Enolonium Species
Herein it is shown,
for the first time, that enolonium species
are powerful electrophiles capable of reacting with aromatic compounds
in an intermolecular manner to afford α-arylated ketones. The
reaction is compatible with a variety of functional groups, is of
wide scope with respect to aromatic compounds and ketone, and even
works for polymerization-prone substrates such as substituted pyrroles,
thiophenes, and furans. Only 1.6 to 5 equiv of the commodity aromatic
substrates is needed