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

Laccase-catalyzed iodination of 4-hydroxybenzoic acid derivatives and related compounds 1q–ta.

graphic file with name c9ra02541c-u22.jpg
Entry 1 Laccase (U) Time(h) Yield products (%)
1 q 45 + 90 36 graphic file with name c9ra02541c-u23.jpg
2b r 45 + 180 120 graphic file with name c9ra02541c-u24.jpg
3c s 45 + 500 48 graphic file with name c9ra02541c-u25.jpg
4 t 45 + 270 24 graphic file with name c9ra02541c-u26.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

Additional enzyme and substrate were added during 10 h.

c

Additional enzyme and substrate were added during 30 h.