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. Author manuscript; available in PMC: 2012 Mar 16.
Published in final edited form as: Org Lett. 2011 Aug 17;13(18):4862–4865. doi: 10.1021/ol201947b

Table 1.

Optimization of Coupling Conditions.a

graphic file with name nihms318038u3.jpg
entry catalyst ligand base yield [%]b
1 CuSO4·5H2O 1,10-phenanthroline K2CO3 38
2 CuSO4·5H2O 1,10-phenanthroline Cs2CO3 59
3 CuSO4·5H2O 1,10-phenanthroline K3PO4 68
4 CuSO4·5H2O 1,10-phenanthroline KOt-Bu
5 CuI DMEDA K3PO4 25c
6 CuCN DMEDA K3PO4 27c
a

Conditions: 15 mol % Cu, 30 mol % ligand, 2 equiv base, toluene (concn = 0.4 M), 95 °C, 24 h.

b

Isolated yields.

c

Reactions run at 110 °C.