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. Author manuscript; available in PMC: 2014 Oct 25.
Published in final edited form as: Angew Chem Int Ed Engl. 2013 Sep 13;52(44):10.1002/anie.201306007. doi: 10.1002/anie.201306007

Table 1.

Cascade amination/amidation: Catalyst identification.[a]

graphic file with name nihms534443u3.jpg
Entry X1 X2 Ligand Yield[b]
1 OTf Cl PPh3 0%
2 OTf Cl PCy3 0%
3 OTf Cl PtBu3 0%
4 OTf Cl L1 trace
5 OTf Cl L2 47%
6 OTf Cl L3 63%
7 OTf Cl L4 77%
8 OTf Cl 2 mol% P1[c] 88% (86%)
9 Br Cl 2 mol% P1[c] 87%
10 Cl Cl 2 mol% P1[c] 70%
[a]

Reaction conditions: aryl halide (0.5 mmol), aniline (0.5 mmol), acetamide (0.65 mmol), (allylPdCl)2 (3 mol%), ligand (3 mol%), Cs2CO3 (1.2 mmol), tBuOH (1.0 mL), 110 °C, 12 h.

[b]

Yield determined by GC using tetradecane as internal standard, isolated yield in parenthesis.

[c]

Precatalyst P1 was used instead of (allylPdCl)2 and ligand.

[c]