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. Author manuscript; available in PMC: 2010 Oct 4.
Published in final edited form as: Org Lett. 2008 Jul 12;10(16):3505–3508. doi: 10.1021/ol801285g

Table 1.

Coupling of Amides With Aryl Chlorides

graphic file with name nihms110642t1.jpg
entrya ArCI amide product yieldb
1 graphic file with name nihms110642t2.jpg graphic file with name nihms110642t3.jpg graphic file with name nihms110642t4.jpg 98%
2 graphic file with name nihms110642t5.jpg graphic file with name nihms110642t6.jpg graphic file with name nihms110642t7.jpg 98%
3 graphic file with name nihms110642t8.jpg graphic file with name nihms110642t9.jpg graphic file with name nihms110642t10.jpg 84%c
4 graphic file with name nihms110642t11.jpg graphic file with name nihms110642t12.jpg graphic file with name nihms110642t13.jpg 83%
5 graphic file with name nihms110642t14.jpg graphic file with name nihms110642t15.jpg graphic file with name nihms110642t16.jpg 95%
[a]

Reaction conditions: 1.5 min preactivation at 110 °C with 4 mol % H2O, 1 mol % Pd(OAc)2, and 3 mol % 2 in 2 mL/mmol of t-BuOH; 1.0 equiv aryl chloride, 1.2 equiv amide, and 1.4 equiv K2CO3.

[B]

Yields represent isolated yields (average of 2 runs).

[c]

1.5 equiv of amide.