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. Author manuscript; available in PMC: 2010 Aug 12.
Published in final edited form as: J Am Chem Soc. 2009 Aug 12;131(31):11049. doi: 10.1021/ja903049z

Table 2.

Determination of the Catalyst Loading Required for the Coupling of Ammonia with ortho-Substituted Aryl Halidesa

graphic file with name nihms131741u2.jpg
entry aryl halide loading (%) concentration [M] T [°C]b t [h] conv. (%)c A:Bd
1 graphic file with name nihms131741t1.jpg 0.5 0.04 80 24 100 >30:1
2 0.25 0.04 80 24 <10 --
3 0.1 0.1 100 24 100 2:1
4 graphic file with name nihms131741t2.jpg 0.1 0.1 100 24 100 17:1
5 graphic file with name nihms131741t3.jpg 0.1 0.1 100 24 100 17:1
a

Reactions conducted with 1:1 ratio of metal to ligand, 0.5 mmol aryl bromide, 5 mL of 0.5 M ammonia solution, 1.4 equiv NaOtBu in 1,4-dioxane.

b

Temperature of bath.

c

Determined by GC analysis.

d

Determined by 1H NMR spectroscopy.