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. Author manuscript; available in PMC: 2012 Dec 2.
Published in final edited form as: Org Lett. 2011 Nov 9;13(23):6320–6323. doi: 10.1021/ol202881q

Table 1.

Optimization for Oxidative Dearomatization

graphic file with name nihms338087u2.jpg
entry conditions yield of 2a
1 Pd(OAc)2 (10 mol %), PhI(OAc)2 (2.0 equiv) PhMe, rt, 12 h 0%
2 Pd(OAc)2 (10 mol %), PhI(OAc)2 (2.0 equiv) CH3CN, rt, 12 h 5–10%
3 Pd(OAc)2 (10 mol %), PhI=O, (3.0 equiv) CH3CN, rt, 12 h N. R.
4 Pd(OAc)2 (10 mol %), Selectfluor (2.0 equiv) CH3CN, rt, 12 h 43%
5 PhI(OAc)2 (1.1 equiv), CH3CN 0%b
6 PhI(O2CCF3)2 (1.1 equiv), (F3C)2CHOH 0%b
a

Isolated yield (%) after purification by chromatography on SiO2;

b

2a was the only isolable product.