Skip to main content
. Author manuscript; available in PMC: 2009 Nov 21.
Published in final edited form as: J Org Chem. 2008 Oct 23;73(22):8851–8860. doi: 10.1021/jo801631v

Table 2.

Palladium-Catalyzed Carboamination of N-Protected γ–Aminoalkenes with Functionalized Aryl Bromidesa

Entry Amine Aryl bromide Product Rxn.
Time (h)
Yield
(%) b
1 graphic file with name nihms-87958-t0003.jpg graphic file with name nihms-87958-t0004.jpg graphic file with name nihms-87958-t0005.jpg 15
11
75
(77) c,e
2 1 graphic file with name nihms-87958-t0006.jpg graphic file with name nihms-87958-t0007.jpg 27
26
82
(81) c,e
3 1 graphic file with name nihms-87958-t0008.jpg graphic file with name nihms-87958-t0009.jpg 20 78 d
4 1 graphic file with name nihms-87958-t0010.jpg graphic file with name nihms-87958-t0011.jpg 18 76 d
5 1 graphic file with name nihms-87958-t0012.jpg graphic file with name nihms-87958-t0013.jpg 28 71
6 graphic file with name nihms-87958-t0014.jpg graphic file with name nihms-87958-t0015.jpg graphic file with name nihms-87958-t0016.jpg 18
15
79
(72) c,e
7 3 graphic file with name nihms-87958-t0017.jpg graphic file with name nihms-87958-t0018.jpg 18 76 d,f
8 graphic file with name nihms-87958-t0019.jpg graphic file with name nihms-87958-t0020.jpg graphic file with name nihms-87958-t0021.jpg 16
18
88
(17)c
9 4 graphic file with name nihms-87958-t0022.jpg graphic file with name nihms-87958-t0023.jpg 18 88 d
a

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.

b

Yield refers to average isolated yield obtained in two or more experiments.

c

NaO tBu was used in place of Cs2CO3 and toluene was used as solvent.

d

The reaction was conducted at 85 °C in DME solvent.

e

Pd2(dba)3 was used in place of Pd(OAc)2.

f

Dppe was used in place of Dpe-phos.