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. Author manuscript; available in PMC: 2014 Jun 5.

Published in final edited form as: J Am Chem Soc. 2013 May 24;135(22):8213–8221. doi: 10.1021/ja403165u

Reaction inhibition of phenol formation with the addition of 100 equiv of Hg at t = 0 ( ) and 4 h ( ) using the following starting substrate: (A) cyclohexanone and (B) cyclohexenone. Lack of Hg (■) addition data is included. Dashed lines indicate cyclohexenone and solid lines indicate phenol formation. Additional time course data is in Figure S7. Reaction conditions: [substrate] = 1 M (0.5 mmol), [Pd(TFA)₂] = 0.05 M (0.025 mmol), [2-Me₂Npy] = 0.1 M (0.05 mmol), [TsOH] = 0.2 M (0.1 mmol), Hg = 500 mg (2.49 mmol), DMSO for V_Total of 0.5 mL, 1 atm O₂, 80 °C.

Inline graphic — Reaction inhibition of phenol formation with the addition of 100 equiv of Hg at t = 0 ( ) and 4 h ( ) using the following starting substrate: (A) cyclohexanone and (B) cyclohexenone. Lack of Hg (■) addition data is included. Dashed lines indicate cyclohexenone and solid lines indicate phenol formation. Additional time course data is in Figure S7. Reaction conditions: [substrate] = 1 M (0.5 mmol), [Pd(TFA)₂] = 0.05 M (0.025 mmol), [2-Me₂Npy] = 0.1 M (0.05 mmol), [TsOH] = 0.2 M (0.1 mmol), Hg = 500 mg (2.49 mmol), DMSO for V_Total of 0.5 mL, 1 atm O₂, 80 °C.