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. 2021 Oct 22;12(43):14641–14646. doi: 10.1039/d1sc04748e

Reaction optimization studies.

graphic file with name d1sc04748e-u1.jpg
Entrya Oxime Temp./hv Base Time Yieldb 8a/%
1 9a 30 °C KOt-Bu 16 h 52
2 9b 30 °C KOt-Bu 16 h 45
3 9c 30 °C KOt-Bu 16 h 38
4 9d 30 °C KOt-Bu 16 h 75
5 9d 30 °C KOH 16 h 38
6 9d 30 °C Cs2CO3 16 h 25
7c 9d 450 nm KOt-Bu 1 h 65
8d 9d 30 °C KOt-Bu 1 h 38
9 9d 30 °C KOt-Bu 1 h 44
10e 9d 30 °C KOt-Bu 16 h 10
11f 9d 30 °C KOt-Bu 16 h <5
12g 9d 30 °C KOt-Bu 16 h 49
a

Reactions performed with 0.1 mmol of aryl bromide 3aBr and 0.2 mmol oxime 9a–d with the stated base (0.2 mmol) in DMSO (0.5 mL) under nitrogen.

b

Determined by 1H NMR spectroscopy against an internal standard (dibromomethane).

c

Under irradiation with 18 W blue LEDs (λmax = 450 nm) and fan cooling.

d

Reaction performed in the dark.

e

Reaction performed in the presence of galvinoxyl (1 equiv.).

f

Reaction performed in the presence of DPPH (1 equiv.).

g

Reaction performed in the presence of TEMPO (2 equiv.).