Table 1. Hydrodechlorination Optimization and Control Reactions.
| entry | DHP | [MeCN] (mM) | base | yield of 2a (%) |
|---|---|---|---|---|
| 1 | I, 1.0 equiv | 50 | Cs2CO3 | 60 |
| 2 | I, 1.2 equiv | 50 | Cs2CO3 | 69 |
| 3 | I, 1.5 equiv | 50 | Cs2CO3 | 75 |
| 4 | I, 1.5 equiv | 62.5 | Cs2CO3 | 78b |
| 5 | I, 1.5 equiv | 62.5 | none | c |
| 6 | I, 1.5 equiv | 62.5 | Cs2CO3 | c,d |
| 7 | II, 1.5 equiv | 62.5 | tBuOKe | 22 |
Yield calculated by 1H NMR using 1,3,5-trimethoxybenzene as an external standard.
Isolated yield.
No reaction.
No light.
2.2 equiv.
