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. Author manuscript; available in PMC: 2014 May 17.
Published in final edited form as: J Org Chem. 2013 Apr 29;78(10):4744–4761. doi: 10.1021/jo400222c

Table 4.

Ligands in the Aromatic Decarboxylation (Scheme 3)a

Entry Ligand (equiv) Solvent Conv. (%)b
1 PPh3 (0.2) 5% DMSO-DMF 65
2 PPh3 (0.2) i-PrOH 56
3 PPh3 (0.2) xylenes 78
4 PPh3 (1.0) 5% DMSO-DMF 3
5 PPh3 (1.0) i-PrOH 8
6 PPh3 (1.0) xylenes 39
7 dppe (0.2) xylenes 75
8 dppp (0.2) xylenes 66
9 dppp (1.0) xylenes 41
10 P(O)(octyl)3 (5.0) 5% DMSO-DMF 71
11 Pyridine 5% DMSO-DMF No Prod
12 Bis-sulfoxidec 5% DMSO-DMF 66
a

Reaction conditions: initial concentration [6] = 0.10 M and [Pd(O2CCF3)2] = 0.020 M, 10 equiv CF3CO2H, 3.0 mL solvent, 70 °C, 24 h.

b

GC monitoring of the formation of 8 with biphenyl as internal standard.

c

Pd(OC2CCF3)2 was replaced with Pd(PhSOCH2CH2SOPh)(OAc)2.