Laccase-catalyzed iodination of 4-hydroxyarylketones and related compounds 1h–pa.
| ||||
|---|---|---|---|---|
| Entry | 1 | Laccase (U) | Time (h) | Yield products (%) |
| 1 | h | 45 + 90 | 15 |
|
| 2 | i | 45 + 90 | 15 |
|
| 3 | j | 45 + 180 | 168 |
|
| 4 | k | 45 + 180 | 15 |
|
| 5 | l | 45 + 225 | 24 |
|
| 6d | m | 45 + 360 | 168 |
|
| 7 | n | 45 + 180 | 60 |
|
| 8e | o | 45 + 360 | 120 |
|
| 9 | p | 45 + 90 | 24 |
|
2 mmol 1 were reacted in 90 mL buffer. The yields of 2 and 4 refer to isolated yields. Initially, 45 U enzyme were added, additionally laccase in buffer was added during 5 h by syringe pump. Substrate in 3 mL DMSO was added by a second syringe pump during the same time the enzyme was added. Substrates with one iodination site were reacted with 3 equiv. KI, substrates with 2 iodination sites were reacted with 4 equiv. KI.
Initially, 1.1 equiv. KI and the substrate were added as solids. No DMSO was used. 180 U enzyme were added during 12 h.
180 mL buffer and 6 equiv. KI were used. 300 U additional enzyme and substrate were added during 5 h.
Additional enzyme and substrate were added during 30 h.
Additional enzyme and substrate were added during 20 h.