Synthesis of 9-monoalkylfluorene derivativesa.
| |||
|---|---|---|---|
| Entry | Alcohol | Product | Isolated yield (%) |
| 1 |
|
|
98 |
| 2 |
|
|
99 |
| 3 |
|
|
96 |
| 4 |
|
|
99 |
| 5b |
|
|
95 |
| 6 |
|
|
99 |
| 7 |
|
|
99 |
| 8 |
|
|
99 |
| 9 |
|
|
99 |
| 10 |
|
|
99 |
| 11b,c |
|
|
99 |
| 12b,c |
|
|
99 |
| 13b,d |
|
|
97 |
| 14b,c |
|
|
99 |
| 15b,c |
|
|
99 |
| 16b,d |
|
|
99 |
| 17b,e,f |
|
|
89 |
| 18b,e,f |
|
|
90 |
| 19g |
|
|
99 |
| 20b,e,f |
|
|
85 |
| 21c |
|
|
99 |
| 22b,e,f |
|
|
81 |
Reaction conditions: fluorene (0.5 mmol), alcohols (1.5 mmol), t-BuOK (0.25 mmol), toluene (4 mL), in N2.
24 h.
t-BuOK (0.375 mmol).
t-BuOK (0.50 mmol).
t-BuOK (0.75 mmol).
140 °C.
2-Bromo-9-fluorene was used.