Table 2.
Aryl Diazonium Scope[a]
| |||
|---|---|---|---|
| entry | R = | yield (%)[b] | ee (%)[c] |
| 1 | H (8a) | 82 | 85 |
| 2 | 3-CF3 (8b) | 70 | 84 |
| 3 | 4-F (8c) | 81 | 85 |
| 4 | 3-OMe (8d) | 81 | 79 |
| 5 | 4-OMe (8e) | 73 | 82 |
| 6 | 3,5-Me (8f) | 79 | 82 |
| 7 | 4-fBu (8g) | 82 | 87 |
| 8 | 4-Ph (8h) | 66 | 85 |
| 9 | 4-OMe, 3-CI (8i) | 80 | 80 |
| 10 | 2-F (8j) | 15 | 94 |
Conditions: 6 (1 equiv, 0.054mmol); aryldiazonium tetrafluoroborate (1.4 equiv); Pd2(dba)3 (0.05 equiv); 7a (0.10 equiv); K2CO3 (2 equiv); solvent (1.6 mL); 24 h.
Isolated yields.
Enantiomeric excess determined by chiral phase HPLC.