Table 1. Control Reactions Describing Deviation from Standard Conditions Using Catalytic Copper and TDGa.
entry | deviation from standard conditions | yield of compound 3aa (%)b |
---|---|---|
1 | none | 67 (68) |
2 | no [Cu] | 0 |
3 | no MnO2 | 17 |
4 | no TDG | 15 |
5 | using TDG1 | 5 |
6 | using TDG2 | 0 |
7 | using TDG3 | 43 |
8 | K2S2O8 as an oxidant (2–10 equiv) | 11–21 |
9 | + K2CO3 (2 equiv) | 70 (68) |
10 | + TEMPO (1 equiv) | 0 |
Reactions were performed on a 0.2 mmol scale with respect to the sulfinate salt.
Yields were determined by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard. Isolated yields are in parentheses. The starting material is volatile; therefore, recovered starting material was not reliably determined.