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.