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. Author manuscript; available in PMC: 2008 Aug 8.
Published in final edited form as: J Org Chem. 2006 Dec 22;71(26):9681–9686. doi: 10.1021/jo0617013

Table 1.

Optimization of Conditions for Cross-Coupling Reaction

graphic file with name nihms60269f2.jpg
entry catalyst system catalyst loading solvent molarity base reaction time isolated yield ratio 5a:6aa
1 PdCl2(dppf)·CH2Cl2 2 mol % THF/H2O (9:1) 0.1 Cs2CO3 22 h 63 100:0
2 PdCl2(dppf)·CH2Cl2 2 mol % i-PrOH/H2O (9:1) 0.1 NEt3 22 h 23 100:0
3 PdCl2(dppf)·CH2Cl2 2 mol % Toluene/H2O (9:1) 0.1 Cs2CO3 22 h -- 20:80
4 PdCl2(dppf)·CH2Cl2 5 mol % THF/H2O (9:1) 0.1 Cs2CO3 18 h 30 100:0
5 Pd(PPh3)4 2 mol % THF/H2O (9:1) 0.1 Cs2CO3 40 h 62 100:0
6 Pd(OAc)2 + 2 equiv PPh3 2 mol % THF/H2O (9:1) 0.1 Cs2CO3 45 h 78 92:8
7 Pd(OAc)2 + 3 equiv PPh3 2 mol % THF/H2O (9:1) 0.1 Cs2CO3 45 h 72 97:3
8 PdCl2(CN)2 + 2 equiv PPh3 2 mol % THF/H2O (9:1) 0.1 Cs2CO3 45 h 69 95:5
9 PdCl2(CN)2 + 3 equiv PPh3 2 mol % THF/H2O (9:1) 0.1 Cs2CO3 45 h 70 96:4
10 PdCl2 + 2 equiv PPh3 2 mol % THF/H2O (9:1) 0.1 Cs2CO3 45 h 72 95:5
11 PdCl2 + 3 equiv PPh3 2 mol % THF/H2O (9:1) 0.5 Cs2CO3 22 h 72 100:0
12 PdCl2 + 2 equiv PPh3 2 mol % THF/H2O (9:1) 0.5 Cs2CO3 22 h 68 100:0
13 PdCl2 + 3 equiv PPh3 2 mol % THF/H2O (9:1) 0.5 K3PO4 22 h 67 92:8
14 PdCl2 + 3 equiv PPh3 2 mol % THF/H2O (9:1) 0.5 KHCO3 22 h 62 82:18
15 PdCl2 + 3 equiv PPh3 2 mol % THF/H2O (9:1) 0.5 K2CO3 22 h 67 97:3
16 PdCl2 + 3 equiv PPh3 2 mol % THF/H2O (9:1) 0.5 pyridine 22 h -- 20:80
17 PdCl2 + 3 equiv PPh3 2 mol % THF/H2O (9:1) 0.5 NEt3 22 h -- 55:45
a

Ratio of 5a:6a in isolated material by GC assay.