Table 2. Effects of Concentrations in the Reaction on the Formation of 3aa.
entry | CDCl3 (mL) | 2a (mM) | CF3SO3H (mM) | time (min) | yield of 3a (%)b | yield of 4a (%)b |
---|---|---|---|---|---|---|
1 | 8.0 | 16 | 0.014 | 30 | 29 | 0 |
2 | 4.0 | 31 | 0.028 | 30 | 31 | 0 |
3 | 3.0 | 42 | 0.038 | 30 | 42 | 0 |
4 | 2.0 | 63 | 0.057 | 30 | 51 | 0 |
60 | 97 | 1 | ||||
5 | 1.0 | 126 | 0.11 | 30 | 33 | 1 |
For the reactions, to a solution of 2a (0.13 mmol, 1.1 equiv) and CF3SO3H (0.00011 mmol, 0.001 equiv) in CDCl3 (indicated volume), 1a (0.11 mmol, 1.0 equiv) was added, and the mixture was heated at 60 °C. See the Supporting Information for details.
Determined by 1H NMR analysis.