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. 2015 Apr 22;6:7011. doi: 10.1038/ncomms8011

Table 5. Syntheses of α-alkyloxyl-α,α-diaryl imine.

graphic file with name ncomms8011-i6.jpg
Entry R1 R2OH Temperature (oC) Product Yield (%)
1 n-C3H7 i-PrOH 0 7a 71
2 Me i-PrOH 10 7b 68
3 n-C4H9 i-PrOH 0 7c 63
4 n-C3H7 CH3OH 10 7d 52
5 n-C3H7 EtOH 10 7e 62
6 n-C3H7 Butan-1-ol 10 7f 58
7 n-C3H7 Butan-2-ol 0 7g 65
8 n-C3H7 Cyclohexanol 10 7h 70
9 n-C3H7 Prop-2-yn-1-ol 25 7i 54
10 n-C3H7 (E)-but-2-en-1-ol 25 7j 46
11* Ph CH3OH 90 7k 66
12* 4-NO2C6H4 CH3OH 90 7l 45
13* 4-acetyl C6H4 CH3OH 90 7m:7m′=1.5:1 41
14* 4-tBuC6H4 CH3OH 90 7n:7n′=1:2 54

Reactions condition: 6 (0.5 mmol), NFSI (2 equiv., 1.0 mmol), R2OH (3 equiv., 1.5 mmol), Cu(acac)2 (5 mol %) in CH3CN (2 ml) under N2 atmosphere for 48 h. Isolated yields.

*Reactions condition: 6 (0.5 mmol), NFSI (2 equiv., 1.0 mmol), CH3OH (3 equiv., 1.5 mmol), CuCN (5 mol %) in CH2Cl2 (2 ml) at 90 °C under N2 atmosphere for 48 h. Isolated yields.

Mixture of two isomers. The ratio was determined by 1H NMR analysis.