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. 2019 May 31;7(13):11267–11274. doi: 10.1021/acssuschemeng.9b00619

Table 2. Direct Synthesis of Primary Amines from Vanillyl Alcohol and (NH4)2CO3 Using Ni/Al2O3–SiO2 As a Catalysta.

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        selectivity/%
entry catalyst amount/mg sub. (mmol)/(NH4)2CO3 (mmol) ratio conversion /% 2m 5m 4m 6m 3′m dimers
1 100 0.5:1 83 52 2 3 0 19 23
2 100 0.25:1 87 54 0 2 1 25 27
3 100 0.5:2 54 50 1 2 0 23 23
4 200 0.5:2 >99 58 (40)b 2 4 0 16 20
5 50 0.5:2 34 56 1 2 0 19 22
6 400 1:4 >99 4 4 55 1 7 29
a

General reaction conditions: general procedure 2, Ni/Al2O3–SiO2 catalyst, vanillyl alcohol substrate, (NH4)2CO3, 3 mL t-amyl alcohol, 140 °C, 18 h; conversion and selectivity were calculated by GC-FID.

b

Isolated yield by column chromatography.