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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 1.

Effects of Precatalysts and Solvents on the Coupling of 4-Bromo-tert-butylbenzene with Ammonia in 0.5 M Solutionsa

graphic file with name nihms131741u1.jpg
entry catalyst loading (%) solvent conc. [M]b conversion (%)c A:Bd
1 Pd(OAc)2/CyPF-t-Bu 0.5 1,4-dioxane 0.038 50 --
2 Pd2(dba)3 / CyPF-t-Bu 0.25e 1,4-dioxane 0.038 100 17:1
3 (CyPF-t-Bu)PdCl2 0.5 1,4-dioxane 0.038 100 7:1
4 (CyPF-t-Bu)PdCl2 2.0 DME 0.038 100 0.7:1.0
5 Pd[P(o-tol)3]2/CyPF-t-Bu 0.5 1,4-dioxane 0.038 100 >30:1
6 Pd[P(o-tol)3]2/CyPF-t-Bu 0.5 DME 0.038 100 0.7:1.0
a

Reactions conducted with 0.5 mmol 4-bromo-tert-butylbenzene, 5 mL of 0.5 M ammonia solutions and 1.4 equiv NaOtBu.

b

Concentration of 4-bromo-tert-butylbenzene.

c

Determined by GC with dodecane as an internal standard.

d

Determined by 1H NMR spectroscopy.

e

Reaction conducted with 0.25 mol % Pd2(dba)3 and 0.5 mol % CyPF-t-Bu.