Skip to main content
. 2018 Jan 8;8(4):1737–1743. doi: 10.1039/c7ra12498h

Screening of catalysts and reaction conditions for amination of allylic alcoholsa.

Entry Catalyst Au amount (mol%) Solvent Time (h) Yieldb (%)
1 Ph3PAuCl 0.5 Dioxane 1.5 67 (85)c
2 3a 0.1 Dioxane 1.5 89
3 3b 0.1 Dioxane 4 90
4 3c 0.1 Dioxane 4 90
5 3d 0.1 Dioxane 1.5 95
6 3a 0.05 Dioxane 7 43
7 3b 0.05 Dioxane 20 38
8 3c 0.05 Dioxane 20 41
9 3d 0.05 Dioxane 1.5 91
10 3d 0.01 Dioxane 8 50
11 3d 0.05 MeCN 1.5 50
12 3d 0.05 MeNO2 3 75
13 3d 0.05 THF 3 Trace
14 3d 0.05 DMF 3 n.r.
15 3d 0.05 DMSO 3 n.r.
16 SBA-PPh2AuCl 0.5 Dioxane 1.5 73
17 PS-PPh2AuCl 0.5 Dioxane 1.5 78
18 AgOTf 0.1 Dioxane 1.5 n.r (29)c
19 2d 0.1 Dioxane 24 n.r
a

Reaction conditions: 1 mmol trans-1,3-diphenyl-2-propen-1-ol, 2 mmol p-toluene sulfonamide, 1 : 1 cat. (mol% Au)/AgOTf, 2 mL solvent, argon atmosphere.

b

Isolated yield.

c

Data in parentheses were yields avoiding light.