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. Author manuscript; available in PMC: 2009 Jun 5.
Published in final edited form as: Org Lett. 2008 May 9;10(11):2207–2210. doi: 10.1021/ol800619c

Table 2.

Arylation of Anilides with Benzene

graphic file with name nihms55905f3.jpg

entry anilide Pd(OAc)2 temp biphenyl yielda
1 graphic file with name nihms55905t1.jpg(1b) 5 mol% 80 °C graphic file with name nihms55905t2.jpg 70% (3b)
2 graphic file with name nihms55905t3.jpg(1c) 5 mol% 90 °C graphic file with name nihms55905t4.jpg 91% (3c)
3 graphic file with name nihms55905t5.jpg (1d) 10 mol% 90 °C graphic file with name nihms55905t6.jpg 84% (3d)
4 graphic file with name nihms55905t7.jpg (1e) 7.5 mol% 80 °C graphic file with name nihms55905t8.jpg 87% (3e)
5 graphic file with name nihms55905t9.jpg (1f) 10 mol% 90 °C graphic file with name nihms55905t10.jpg 86% (3f)
6 graphic file with name nihms55905t11.jpg (1g) 10 mol% 100 °C graphic file with name nihms55905t12.jpg 68%b (3g)
7 graphic file with name nihms55905t13.jpg (1h) 10 mol% 55°C graphic file with name nihms55905t14.jpg 59%a,c (3h)
a

Isolated yield, average of two runs.

b

Incomplete conversion of the starting material.

c

Reaction run for 96 h.