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12. Representative experimental procedure: Phenylboronic
acid (122 mg, 1.0 mmol, 1 equiv.) was mixed with water
in the reaction flask (10.0 mL, 0.1 M solution) and rapid
stirring was begun (Note: with reactions using PTC, a
stock 0.1 M aqueous solution was added here instead).
Into the solution was added NaOAc (272 mg, 2.0 mmol,
2 equiv.) and Pd(OAc)2 (11 mg, 0.05 mmol, 0.05 equiv.).
A balloon of O2 was placed over the neck of the flask and
the solution was stirred at room temperature for 3 h. The
mixture was then diluted with 1:1 hexanes/EtOAc (10
mL), extracted with 1:1 hexanes/EtOAc (3×20 mL), then
washed with H2O (10 mL). The organic layer was concen-
trated in vacuo, and subjected to flash chromatography
(30 g SiO2, eluted with 10:1 hexanes/EtOAc) to afford
biphenyl (73 mg, 95%).
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14. For mechanistic considerations of the oxidative dimeriza-
tion of boronic acids and formation of side products, see:
Ref. 7b.