Table 3.
Entry | Reagent | Solvent | T (°C) | t (h) | Product | ee (%) |
1 | F–TEDA | MeCN | 0 | 0.3 | 6-F | 86 |
2 | F–TEDA | MeCN | rt | 0.15 | 6-F | 88 |
3 | F–TEDA | MeCN | 50 | <0.3 | 6-F | 79 |
4 | NFSI | CH2Cl2 | −25 | –b | 6-F | 89b |
5 | NFSI | CH2Cl2 | 0 | 19 | 6-F | 91 |
6 | NFSI | CH2Cl2 | rt | 10 | 6-F | 87.5 |
7 | NCS | MeCN | rt | 0.5 | 6-Cl | 82 |
8 | NCS | CH2Cl2 | 0 | 7 | 6-Cl | 90 |
aReactions were run to complete conversion (TLC), unless otherwise mentioned. bAnalysis at 15% conversion. Complete conversion occurred after warming to rt.