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. Author manuscript; available in PMC: 2010 Feb 16.
Published in final edited form as: J Am Chem Soc. 2008 Apr 30;130(20):6586. doi: 10.1021/ja077074w

Scheme 1.

Scheme 1

Comparison of the Reactivity of Aryl Chlorides vs. Aryl Bromides and Aryl Bromides vs. Aryl Iodides in the Presence of Pd(OAc)2 and CyPF-t-Bu (1:1).

Reagents and conditions: a Isolated Yield. i. 0.01 mol % Pd(OAc)2, 0.01 mol % CyPF-t-Bu, 1.4 equiv. NaOtBu, DME, 100 °C, 10 h; ii. 0.005 mol % Pd(OAc)2, 0.005 mol % CyPF-t-Bu, 1.4 equiv. NaOtBu, DME, 100 °C, 20 h; iii. 0.05 mol % Pd(OAc)2, 0.05 mol % CyPF-t-Bu, 1.4 equiv. NaOtBu, DME, 100 °C, 20 h; 0.5 mol % Pd(OAc)2, 0.5 mol % CyPF-t-Bu, 1.4 equiv. NaOtBu, DME, 100 °C, 20 h.