Table 1. Reaction Optimization Conditionsa.
entry | deviation in conditions | yield (%) |
---|---|---|
1 | standard conditions | 79 (63%) |
2 | 2 equiv Zn(0) | 21 |
3 | 2 equiv Mn(0) | 24 |
4 | 2 equiv TDAE | 43 |
5 | no reductant | <1 |
6 | diethylzinc bromide | <1 |
7 | phenethylzinc bromide | 58 |
8 | no additives | 49 |
9 | dioxanylzinc bromide | 56 |
10 | cyclopropylzinc bromide | 59 |
11 | tert-butylzinc bromide | 46 |
12 | 1-ethylpropylzinc bromide | 70 |
13 | DMF instead of NMP | 66 |
14 | DMSO instead of NMP | 70 |
15 | toluene instead of NMP | 25 |
16 | THF instead of NMP | 29 |
17 | MeCN instead of NMP | 0 |
0.1 mmol scale reactions in 0.5 mL of solvent.1H NMR yields using pyrene as an internal standard. The value in parentheses is the isolated yield [diastereomeric ratio (dr) = 1:1] from 0.5 mmol. The dr was determined by 1H NMR of the crude reaction mixture.