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. Author manuscript; available in PMC: 2010 Dec 23.
Published in final edited form as: Org Biomol Chem. 2010 Jul 19;8(18):4066–4070. doi: 10.1039/c0ob00182a

Table 1.

Coupling of model biphenyl triflate 13 to afford model biphenyl boronic ester 14.

graphic file with name nihms239144u1.jpg
Entry R [Pd] cat. Ligand Base Solvent Temp (°C) Time (h) %Yielda
1 Bpin Pd(dppf)Cl2 -- KOAc dioxane 80 26 0%
2 Bpin Pd(OAc)2 CyJohnPhos KF toluene 100 17 0%
3 H Pd(PPh3)4 -- Et3N dioxane 80 4 0%
4 H Pd(dppf)Cl2 -- Et3N dioxane 70 27 0%
5 Bpin Pd(OAc)2 SPhos K3PO4 toluene 100 15 28%
6 Bpin Pd(OAc)2 SPhos K3PO4 toluene 130 16 14%
7 Bpin Pd2(dba)3·CHCl3 SPhos K3PO4 toluene 110 17 66%
a

Yield was determined by mass balance after silica gel column chromatography.