Table 1. The effect of base a .
| ||||
Entry | Base |
3aa
|
Recovery of 1a b (%) | |
Yield b (%) | ee c (%) | |||
1 d | Na2CO3 | 4 | n.d. e | 85 |
2 | K2CO3 | 42 | 51 | 43 |
3 | Rb2CO3 | 67 | 66 | 27 |
4 | Cs 2 CO 3 | 77 | 72 | 6 |
5 | Na3PO4 | 47 | 58 | 37 |
6 | K3PO4 | 66 | 71 | 16 |
7 | LiOH | 36 | 42 | 47 |
8 | NaOH | 64 | 45 | 19 |
9 | KOH | 27 | 62 | 47 |
10 | LiOtBu | 37 | 31 | 25 |
11 | TEA | 3 | n.d. e | 71 |
aUnless indicated otherwise, the experiments were performed with 1a (0.2 mmol), 2a (0.24 mmol), Pd2(dba)3·CHCl3 (0.005 mmol), L10 (0.015 mmol), and base (0.4 mmol) in DCE (2 mL) at 80 °C under Ar atmosphere.
bThe yield and recovery were determined by 1H NMR analysis using 1,3,5-trimethylbenzene as the internal standard.
cThe ee values were determined by HPLC analysis.
dReaction time: 22.5 h.
en.d. = not determined.