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. Author manuscript; available in PMC: 2009 Oct 3.
Published in final edited form as: J Org Chem. 2008 Aug 30;73(19):7481–7485. doi: 10.1021/jo801269m

Table 3.

Optimization of Reaction Conditions for Heteroaryl Chloridesa

graphic file with name nihms86313f4.jpg
entry catalyst/ligand (mol %) base solvent (°C) ratio 4a/3aa
1 Pd(OAc)2/XPhos (3/6) K2CO3 THF/H2O (80) 72/28
2 Pd(OAc)2/XPhos (3/6) K2CO3 CPME/H2O (100) 77/23
3 Pd(OAc)2/RuPhos (3/6) Cs2CO3 THF/H2O (80) 46/54
4 Pd(OAc)2/DavePhos (3/6) Cs2CO3 THF/H2O (80) 0/100
5 Pd(OAc)2/SPhos (3/6) Cs2CO3 THF/H2O (80) 0/100
6 Pd(OAc)2/XantPhos (3/6) Cs2CO3 THF/H2O (80) 90/10
7 Pd(OAc)2/(S)-BINAP (3/6) Cs2CO3 THF/H2O (80) 0/100
8 Pd(OAc)2/n-BuPAd2 (3/6) Cs2CO3 Toluene/H2O (100) 100/0
a

Ratio of product/starting material as determined by GC-MS assay.