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. Author manuscript; available in PMC: 2011 Jun 26.
Published in final edited form as: Tetrahedron. 2010 Jun 26;66(26):4811–4815. doi: 10.1016/j.tet.2010.03.111

Table 1.

Arylation of N-phenylpivalamidesa, b

graphic file with name nihms195023u1.jpg
Entry Ar base yield (%)
sm mono di tri
1 Ph none 100 0 0 0
2 graphic file with name nihms195023t1.jpg Cs2CO3 91 7 2 0
3 Cs2CO3 39 41 12 8
4 graphic file with name nihms195023t2.jpg none 100 0 0 0
5 Cs2CO3 12 32 40 16
a

Reaction conditions: 0.2 mmol substrate, 10 mol% Pd(OAc)2, 4 equiv AgOAc, 1.2 equiv Cs2CO3, 0.5 mL iodobenzene, 130°C,3 h, air.

b

Yield was determined by 1H NMR analysis of crude product using CH2Br2 as the internal standard.