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. Author manuscript; available in PMC: 2012 Apr 1.
Published in final edited form as: Org Lett. 2011 Mar 10;13(7):1852–1855. doi: 10.1021/ol2003572

Table 1.

Optimization of C-H Alkylation

graphic file with name nihms280321u2.jpg
entry oxidant additive solvent GCMS conversion
1 Mn(OAc)3 H2SO4 AcOH:H2O 1:1 71%
2 Cu(OAc)2 H2SO4 AcOH:H2O 1:1 1%
3 KMnO4 H2SO4 AcOH:H2O 1:1 20%
4 Ce(SO4)2 H2SO4 AcOH:H2O 1:1 54%
5 K2Cr2O7 H2SO4 AcOH:H2O 1:1 26%
6 Fe(SO4)2•7H2O H2SO4 AcOH:H2O 1:1 6%
7 (NH4) 2S2O7 H2SO4 AcOH:H2O 1:1 12%
8 benzoquinone H2SO4 AcOH:H2O 1:1 3%
9 Mn(OAc)3 H2SO4 AcOH:H2O 1:1 6%
10 Mn(OAc)3 TFA AcOH:H2O 1:1 78% (60%)a
11 Mn(OAc)3 TFAb AcOH:H2O 1:1 71%
12 Mn(OAc)3 KHF2 AcOH:H2O 1:1 71%
13 Mn(OAc)3 - AcOH:H2O 1:1 65%
14 Mn(OAc)3 TFA AcOH 48%
15 Mn(OAc)3 TFA DMSO 4%
16 Mn(OAc)3 TFA CH3CN 41%
17 Mn(OAc)3 TFA MeOH 54%
18 Mn(OAc)3 TFA ClCH2CH2Cl 51%
19 Mn(OAc)3 TFA acetone 31%
a

Reaction performed at room temperature.

b

Reaction performed with only 0.2 equiv of trifluoroacetic acid.