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. 2023 May 9;26(6):106834. doi: 10.1016/j.isci.2023.106834

Table 1.

Conversion of β-O-4 model compound 1a with 2-aminopyridine 2a at different conditions

Inline graphic
Entrya Iodine Source Solvent 3a Yield (%) 4a Yield (%) 5a Yield (%)
1 – EtOAc/H2O 0.0 95.3 92.6
2 KI EtOAc/H2O 0.0 94.8 85.1
3 CuI EtOAc/H2O 0.0 95.7 89.7
4 KIO3 EtOAc/H2O 31.5 96.1 trace
5 NaIO3 EtOAc/H2O 23.4 94.7 trace
6 KIO4 EtOAc/H2O 28.8 96.4 trace
7 NaIO4 EtoAc/H2O 26.6 96.0 trace
8 I2 EtOAc/H2O 40.0 95.3 –
9 I2 CH2Cl2/H2O 2.3 45.6 14.3
10 I2 t-AmOH/H2O 10.8 38.1 16.5
11 I2 CH3CN/H2O 22.0 60.1 36.0
12 I2 THF/H2O 33.6 65.0 38.5
13 I2 Toluene/H2O 60.5 96.8 –
a

Reaction conditions: Step 1: 1a (0.2 mmol), 5 wt% Pd/C (5 mol%), NaBH4 (10 mol%) in water (0.5 mL), toluene (1.5 mL), 140°C, t = 2 h. Step 2: 2a (0.4 mmol), iodine source (0.35 mmol), 140°C, t = 15 h. Yield was determined by GC-FID using dodecane as an internal standard.