Table 1. Optimization of Reaction Conditionsa.
entry | variation from initial conditionsa | yieldb (%) |
---|---|---|
1 | none | 62 |
2 | 0.16 M instead of 0.08 M | 47c |
3 | 5 h instead of 3 h | 20 |
4 | 4 Å MS as an additive | 53 |
5 | AgPF6 (1.5 equiv) as an additive | 23d |
6 | TFA (1:4 v/v with THF) as an additive | 25d |
7 | TEMPO (10 mol %) as an additive | 25d |
8 | MeCN instead of THF | 37e |
9 | DMF instead of THF | 38 |
10 | CH2Cl2 instead of THF | 55 |
11 | MeOH/THF(1:1v/v, 0.08 M) | 91 |
12 | without current | nr |
Initial conditions: undivided cell, Pt cathode, C-SK50 anode, constant current = 10 mA, 1 (0.4 mmol), nBu4PF6 (1.0 equiv), MeOH (10 equiv), THF (0.08 M), rt, 3 h.
Isolated yield.
50% conversion.
Partial decomposition was observed.
59% conversion.