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. 2019 Apr 2;9(18):10340–10344. doi: 10.1039/c9ra01481k

Optimization of the reaction conditionsa.

graphic file with name c9ra01481k-u1.jpg
Entry Solvent Oxidant Time (h) Temp (°C) Yield (%)
1 DMSO SF 24 100 71, 15b, 65c
2 DMF SF 24 100 23
3 DMAC SF 24 100 Trace
4 Toluene SF 24 100 0
5 NMF SF 24 100 18
6 DMSO (NH4)2S2O8 24 100 Trace
7 DMSO K2S2O8 24 100 33
8 DMSO 24 100 0
9 DMSO SF 48 100 73
10 DMSO SF 16 100 46
11 DMSO SF 8 100 23
12 DMSO SF 4 100 Trace
13 DMSO SF 24 120 67
14 DMSO SF 24 80 56
15 DMSO SF 24 60 29
16 DMSO SF 24 40 0
a

Reaction conditions: 1a (1 mmol), 2 (1 mmol), oxidant (1.1 mmol) and DMSO (3 mL) in a sealed tube at the indicated reaction conditions.

b

Reaction under N2.

c

Reaction was performed on a 10 mmol scale of 1a.