Table 1. Effect of Additivesa.
yield
(%)b |
|||
---|---|---|---|
entry | additive | 2a | 3 |
1 | LiBr | 0 | 72 (67)c |
2 | − | 78 (70)c | 0 |
3 | LiCl | 0 | 13 |
4d | n-Bu4NBr | 0 | 34 |
5e | n-Bu4NCl | 0 | 50 |
6 | n-Bu4NHSO4 | 0 | 13 |
7 | NaBr | 0 | 26 |
8 | KBr | 0 | 23 |
9 | LiBF4 | 41 | 0 |
All reactions were conducted with 0.194 mmol of 1 in DME (1.0 mL).
Determined by 1H NMR analysis using an internal standard.
Isolated yield is given in parentheses.
Ynone 1 was recovered in 29% yield.
Ynone 1 was recovered in 25% yield.