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. Author manuscript; available in PMC: 2009 Aug 21.
Published in final edited form as: Org Lett. 2007 Jul 25;9(17):3279–3282. doi: 10.1021/ol071241f

Table 1.

Optimization Studies

graphic file with name nihms-123260-t0007.jpg
entry ligandb conversion (%)c product ratiod isolated yield
1 dppee 50 68:0:32 —
2 Dpe-Phos 97 56:23:21 —
3 Xantphos 82 50:35:15 —
4 P(o-tol)3 87 9:17:74 —
5 P(2-furyl)3 97 71:7:21 62%e
a

Conditions: 1.0 equiv 1a, 1.2 equiv Ar1Br, 1.2 equiv NaOtBu, 1 mol % Pd2(dba)3, 4 mol % chelating ligand or 8 mol % monodentate ligand, toluene (0.2 M), 105 °C, 8 h.

b

Dppe = 1,2-bis(diphenylphosphino)ethane, Dpe-Phos = 1,1-bis(diphenylphosphinophenyl)ether, Xantphos = 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene.

c

Conversion refers to % starting material consumed; 9-11 were the sole products detected in the crude reaction mixture.

d

Determined by 1H NMR analysis of crude reaction mixtures.

e

This yield was obtained after complete conversion.