Phenyl[2-(trimethylsilyl)phenyl]iodonium Trifluoromethanesulfonate

Used Chemicals

• Phenyl[2-(trimethylsilyl)phenyl]iodonium Triflate [P1620]
• Tetraphenylcyclopentadienone [T1062]
• Tetrabutylammonium Fluoride (= TBAF) (ca. 1mol/L in Tetrahydrofuran) [T1338]
• Dichloromethane

Procedure

To a solution of phenyl[2-(trimethylsilyl)phenyl]iodonium triflate (402 mg, 0.80 mmol) in CH₂Cl₂ (10 mL) was added tetraphenylcyclopentadienone (1.54 g , 4.0 mmol) under nitrogen and was cooled to 0 ˚C. TBAF (ca. 1mol/L solution in Tetrahydrofuran, 0.96 mL, 0.96 mmol) was added　and the mixture was stirred at room temperature for 30 min. The reaction was quenched with water and extracted with CH₂Cl₂. The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the crude was purified by column chromatography (ethyl acetate:hexane = 1:99 on silica gel) to give 1 as a white solid (296 mg, 86% yield).

Experimenter’s Comments

The reaction mixture was monitored by TLC (ethyl acetate: hexane = 1:99, Rf = 0.55).
This experiment was operated in a fume hood due to the generation of carbon monoxide.

Analytical Data

1,2,3,4-Tetraphenylnaphthalene (1)

¹H NMR (270 MHz, CDCl₃); δ 7.67-7.63 (m, 2H), 7.41-7.38 (m, 2H), 7.26-7.19 (m, 10H), 6.89-6.82 (m, 10H).

Lead Reference

• A New and Efficient Hypervalent Iodine-Benzyne Precursor, (Phenyl)[o-(trimethylsilyl)phenyl]iodonium Triflate: Generation, Trapping Reaction, and Nature of Benzyne
• T. Kitamura, M. Yamane, K. Inoue, Mi. Todaka, N. Fukatsu, Z. Meng, Y. Fujiwara, J. Am. Chem. Soc. 1999, 121, 11674.

References

• T. Kitamura, M. Yamane, J. Chem. Soc., Chem. Commun. 1995, 983.
• T. Kitamura, M. Yamane, K. Inoue, M. Todaka, N. Fukatsu, Z. Meng, Y. Fujiwara, J. Am. Chem. Soc. 1999, 121, 11674.
• K. Okuma, T. Yamamoto, T. Shirokawa, T. Kitamura, Y. Fujiwara, Tetrahedron Lett. 1996, 37, 8883.
• T. Kitamura, M. Todaka, Y. Fujiwara, Org. Synth. 2002, 78, 104.