Table 2.
Entry | Allenyne | Product | 4/5[b] | Yield of4[%],[c] ratio[b] |
---|---|---|---|---|
1 | 10:1 | 73 | ||
2 | 99:1 | 92 | ||
3 | 99:1 | 55 4 c/4 c′=2.4:1 | ||
4 | 9:1 >11:1 | 81 92[d] | ||
5 | 18:1 | 65 4 e/4 e′=2.3:1 | ||
6 | 5:1 | 48 4 f/4 f′=1.4:1 | ||
7 | >20:1 | 57 |
Unless otherwise noted, 1 (0.1–0.2 mmol), B2pin2 (1.3 equiv), Pd(OAc)2 (2 mol %), BQ (1.1 equiv), and LiOAc⋅2 H2O (20 mol %) were dissolved in DCE (5 mL mmol−1) and stirred at 50 °C for 15 h.
The ratio was determined by 1H NMR analysis of the reaction mixture.
Yield of the isolated product.
1 mmol of 1 d was used. E=CO2Me.