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. 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 3.

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

Entry Amine Aryl bromide Product dr Rxn.
Time (h)		 Yield
(%) b
1 graphic file with name nihms-87958-t0024.jpg graphic file with name nihms-87958-t0025.jpg graphic file with name nihms-87958-t0026.jpg 12:1 20 80
2 graphic file with name nihms-87958-t0027.jpg graphic file with name nihms-87958-t0028.jpg graphic file with name nihms-87958-t0029.jpg 15:1 16 76
3 14 graphic file with name nihms-87958-t0030.jpg graphic file with name nihms-87958-t0031.jpg 14:1 18 73
4 graphic file with name nihms-87958-t0032.jpg graphic file with name nihms-87958-t0033.jpg graphic file with name nihms-87958-t0034.jpg >20:1 16 75
5 graphic file with name nihms-87958-t0035.jpg graphic file with name nihms-87958-t0036.jpg graphic file with name nihms-87958-t0037.jpg >20:1 18 74
6 graphic file with name nihms-87958-t0038.jpg graphic file with name nihms-87958-t0039.jpg graphic file with name nihms-87958-t0040.jpg >20:1 23
18		 71
(62) c,d
7 17 graphic file with name nihms-87958-t0041.jpg graphic file with name nihms-87958-t0042.jpg >20:1 20 73
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 °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

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