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. Author manuscript; available in PMC: 2009 Oct 15.
Published in final edited form as: J Am Chem Soc. 2008 Sep 18;130(41):13552–13554. doi: 10.1021/ja8055358

Table 1.

Screen of Ligands and Pd Sources for the Coupling of Aniline and 4-t-Butylphenyl Methanesulfonatea

graphic file with name nihms110657t1.jpg
Entry Ligand Pd Source Yieldc
1 1 Pd2(dba)3 0%
2 1 6 98%
3b 1 Pd(OAc)2 99%
4 2 7 4%
5b 2 Pd(OAc)2 2%
6 3 8 0%
7b 4 Pd(OAc)2 0%
8b 5 Pd(OAc)2 0%
a

ArOMs (1mmol), amine (1.2 mmol), Pd (1 mol%), ligand (2 mol%), K2CO3 (1.4 mmol), t-BuOH (12 mL/mmol), 110 °C, 3 h.

b

Using water activation protocol (ref. 9c).

c

GC Yields.