Table 2.
Entry | Amine | Aryl bromide | Product | Rxn. Time (h) |
Yield (%) b |
---|---|---|---|---|---|
1 | 15 11 |
75 (77) c,e |
|||
2 | 1 | 27 26 |
82 (81) c,e |
||
3 | 1 | 20 | 78 d | ||
4 | 1 | 18 | 76 d | ||
5 | 1 | 28 | 71 | ||
6 | 18 15 |
79 (72) c,e |
|||
7 | 3 | 18 | 76 d,f | ||
8 | 16 18 |
88 (17)c |
|||
9 | 4 | 18 | 88 d |
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), 100–105 °C.
Yield refers to average isolated yield obtained in two or more experiments.
NaO tBu was used in place of Cs2CO3 and toluene was used as solvent.
The reaction was conducted at 85 °C in DME solvent.
Pd2(dba)3 was used in place of Pd(OAc)2.
Dppe was used in place of Dpe-phos.