Abstract
A range of symmetric and unsymmetric diaryliodonium triflates
have been prepared employing urea-hydrogen peroxide as the
oxidizing agent. The use of aqueous hydrogen peroxide and catalytic
systems with methylrhenium trioxide in the oxidation of iodoarenes
has also been investigated.
Key words
hypervalent iodine - diaryliodonium salts - oxidation - arenes - green chemistry
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Diphenyliodonium
Triflate (1a) : A stirred mixture of CH2 Cl2 and
TFE (2:1, 1 mL) was cooled to 0 ˚C and UHP (47 mg, 0.50
mmol) was added. Tf2 O (168 µL, 1.00 mmol) was
added dropwise to the suspension and the mixture was stirred for
30 min at 0 ˚C. Iodobenzene (28 µL, 0.25 mmol) was
added, followed by benzene (45 µL, 0.50 mmol) and the solution
was warmed to r.t., then heated at 40 ˚C for 3 h. The mixture
was allowed to cool to r.t., evaporated in vacuo and the residue
was purified by trituration with Et2 O (3 × 2
mL), then dried in vacuo to afford the title compound (82 mg, 76%)
as an off-white amorphous solid, spectroscopically identical with
literature data.6
(
p
-Tolyl)(phenyl)iodonium
Triflate (1h) : Prepared according to the above procedure. The
crude reaction mixture was allowed to cool to r.t., evaporated in
vacuo and the residue was partitioned between CH2 Cl2 (5
mL) and H2 O (5 mL). The aqueous layer was further extracted
with CH2 Cl2 (5 mL) and the organic extracts
were combined and evaporated in vacuo. The residue was purified
by trituration with Et2 O (3 × 2 mL) and dried
in vacuo to afford the title compound (84 mg, 76%) as an
off-white amorphous solid, spectroscopically identical with literature
data.6
