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. Author manuscript; available in PMC: 2009 Oct 6.
Published in final edited form as: Org Lett. 2007 Feb 1;9(3):457–460. doi: 10.1021/ol062808f

Table 2.

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

entry amine aryl bromide product dr yieldb
1 graphic file with name nihms-63833-t0005.jpg graphic file with name nihms-63833-t0006.jpg graphic file with name nihms-63833-t0007.jpg 75
2 graphic file with name nihms-63833-t0008.jpg graphic file with name nihms-63833-t0009.jpg 82
3 graphic file with name nihms-63833-t0010.jpg graphic file with name nihms-63833-t0011.jpg 78e
4 graphic file with name nihms-63833-t0012.jpg graphic file with name nihms-63833-t0013.jpg 76e
5 graphic file with name nihms-63833-t0014.jpg graphic file with name nihms-63833-t0015.jpg graphic file with name nihms-63833-t0016.jpg 79
6 graphic file with name nihms-63833-t0017.jpg graphic file with name nihms-63833-t0018.jpg 76c,e
7 graphic file with name nihms-63833-t0019.jpg graphic file with name nihms-63833-t0020.jpg graphic file with name nihms-63833-t0021.jpg 88
17d
8 graphic file with name nihms-63833-t0022.jpg graphic file with name nihms-63833-t0023.jpg graphic file with name nihms-63833-t0024.jpg 88e
9 graphic file with name nihms-63833-t0025.jpg graphic file with name nihms-63833-t0026.jpg graphic file with name nihms-63833-t0027.jpg 12:1 80
10 graphic file with name nihms-63833-t0028.jpg graphic file with name nihms-63833-t0029.jpg graphic file with name nihms-63833-t0030.jpg 15:1 76
11 graphic file with name nihms-63833-t0031.jpg graphic file with name nihms-63833-t0032.jpg graphic file with name nihms-63833-t0033.jpg >20:1 75
12 graphic file with name nihms-63833-t0034.jpg graphic file with name nihms-63833-t0035.jpg graphic file with name nihms-63833-t0036.jpg >20:1 74
13 graphic file with name nihms-63833-t0037.jpg graphic file with name nihms-63833-t0038.jpg graphic file with name nihms-63833-t0039.jpg >20:1 71
14 graphic file with name nihms-63833-t0040.jpg graphic file with name nihms-63833-t0041.jpg >20:1 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

Dppe used in place of Dpe-phos.

d

NaOtBu used in place of Cs2CO3.

e

The reaction wasconducted at 85 °C in DME solvent.