Table 2.
entry | amine | aryl bromide | product | dr | yieldb |
---|---|---|---|---|---|
1 | 75 | ||||
2 | 82 | ||||
3 | 78e | ||||
4 | 76e | ||||
5 | 79 | ||||
6 | 76c,e | ||||
7 | 88 17d |
||||
8 | — | 88e | |||
9 | 12:1 | 80 | |||
10 | 15:1 | 76 | |||
11 | >20:1 | 75 | |||
12 | >20:1 | 74 | |||
13 | >20:1 | 71 | |||
14 | >20:1 | 73 |
Conditions: 1.0 equiv amine, 1.2 equiv ArBr, 2.3 equiv Cs2CO3, 2 mol % Pd(OAc)2, 4 mol % Dpe-phos, dioxane (0.2–0.25 M), 100 °C.
Yield refers to average isolated yield obtained in two or more experiments.
Dppe used in place of Dpe-phos.
NaOtBu used in place of Cs2CO3.
The reaction wasconducted at 85 °C in DME solvent.