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. Author manuscript; available in PMC: 2013 Aug 22.
Published in final edited form as: J Org Chem. 2008 Aug 20;73(18):7175–7180. doi: 10.1021/jo800936h

Table 2.

Optimization of the Palladium-Catalyzed Carbonylative Cyclization of Methyl 2-Iodobenzoate and Benzylamine with dppp as the Ligand (eq 1)a

entry Pd(OAc)2
(mol %)		 dppp
(mol %)		 Cs2CO3
(equiv)		 solvent time
(h)		 temp
(°C)		 %
yieldb
1 10 20 2.0 CH3CN 24 75 0
2 10 20 2.0 CH3OH 24 60 0
3 10 20 2.0 DMSO 24 95 ~5c
4 10 20 2.0 DMF 24 95 ~5c
5 10 20 2.0 CH3NO2 24 95 10
6 10 20 2.0 THF 24 60 42
7 10 20 2.0 PhCH3 24 80 79
8 10 10 2.0 PhCH3 24 95 76
9 5 10 2.0 PhCH3 24 95 89
10 2 4 2.0 PhCH3 24 95 78
11 2 10 2.0 PhCH3 24 95 49
12 5 20 2.0 PhCH3 24 95 53
13 5 10 1.5 PhCH3 24 95 73
14 5 10 3.0 PhCH3 24 95 90
15 5 10 2.0 PhCH3 12 95 78
a

Representative procedure: methyl 2-iodobenzoate (0.5 mmol), benzylamine (1.2 equiv), Pd(OAc)2, dppp, Cs2CO3, and the solvent (6 mL) were placed in a 4 dram vial. The vial was sealed and flushed with CO. The reaction was then stirred at 95 °C for the indicated time with a CO balloon on top of the vial.

b

Isolated yields.

c

GC yields.