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. 2019 Jun 21;9(34):19549–19559. doi: 10.1039/c9ra02541c

Laccase-catalyzed iodination of 4-hydroxyarylketones and related compounds 1h–pa.

graphic file with name c9ra02541c-u12.jpg
Entry 1 Laccase (U) Time (h) Yield products (%)
1 h 45 + 90 15 graphic file with name c9ra02541c-u13.jpg
2 i 45 + 90 15 graphic file with name c9ra02541c-u14.jpg
3 j 45 + 180 168 graphic file with name c9ra02541c-u15.jpg
4 k 45 + 180 15 graphic file with name c9ra02541c-u16.jpg
5 l 45 + 225 24 graphic file with name c9ra02541c-u17.jpg
6d m 45 + 360 168 graphic file with name c9ra02541c-u18.jpg
7 n 45 + 180 60 graphic file with name c9ra02541c-u19.jpg
8e o 45 + 360 120 graphic file with name c9ra02541c-u20.jpg
9 p 45 + 90 24 graphic file with name c9ra02541c-u21.jpg
a

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.

b

Initially, 1.1 equiv. KI and the substrate were added as solids. No DMSO was used. 180 U enzyme were added during 12 h.

c

180 mL buffer and 6 equiv. KI were used. 300 U additional enzyme and substrate were added during 5 h.

d

Additional enzyme and substrate were added during 30 h.

e

Additional enzyme and substrate were added during 20 h.