COMMUNICATIONS
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Representative Procedure for the Aerobic Oxidative
Intramolecular Coupling of o-Terphenyl: 2,3,6,7-
Tetramethoxytriphenylene (2a)
5% Pd/Al2O3 (21 mg, 0.010 mmol) was added to a solution
of 3,3’’,4,4’’-tetramethoxy-o-terphenyl (70 mg, 0.20 mmol) in
2,2,2-trifluoroethanol
(1.0 mL)
and
TfOH
(35 mL,
0.40 mmol). The mixture was stirred at room temperature
under O2 (balloon) for 5 min. 3M NaOH was added and the
resulting mixture was extracted with EtOAc, washed with
brine, dried over MgSO4, filtered, and the solvent was
evaporated to afford the crude product, which was purified
by silica gel column chromatography (EtOAc/hexane, 1/5)
to afford triphenylene 2a; yield: 69 mg.
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Acknowledgements
This work was partially supported by JSPS KAKENHI
Grant Number (No.16H01157, No.26293004), Science and
Technology Research Promotion Program for Agriculture,
forestry, fisheries and food industry (M.S.), the Asahi Glass
Foundation (K.M.), and the Cooperative Research Program
of the Network Joint Research Center for Materials and Devi-
ces.
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[16] One of the reasons for its poor recyclability is likely
the partial degradation of Al2O3 in strongly acidic con-
ditions. Actually, we visually observed the gradual deg-
radation of Al2O3 under the reaction conditions to
form an aggregate, which seemed to be inactive as a cat-
alyst.
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