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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 2.

Coupling of Electron-Deficient Anilines

graphic file with name nihms110642t17.jpg

entrya ArCI aniline product yieldb
1 graphic file with name nihms110642t18.jpg graphic file with name nihms110642t19.jpg graphic file with name nihms110642t20.jpg 94%
2 graphic file with name nihms110642t21.jpg graphic file with name nihms110642t22.jpg graphic file with name nihms110642t23.jpg 86%c
3 graphic file with name nihms110642t24.jpg graphic file with name nihms110642t25.jpg graphic file with name nihms110642t26.jpg 86%
4 graphic file with name nihms110642t27.jpg graphic file with name nihms110642t28.jpg graphic file with name nihms110642t29.jpg 93%
5 graphic file with name nihms110642t30.jpg graphic file with name nihms110642t31.jpg graphic file with name nihms110642t32.jpg 95%
6 graphic file with name nihms110642t33.jpg graphic file with name nihms110642t34.jpg graphic file with name nihms110642t35.jpg 92%d
[a]

Reaction conditions: 1 min preactivation at 110 °C with 4 mol % H20, 1 mol % Pd(OAc)2, and 3 mol % 1 in 2 mL/mmol of t-BuOH; 1.0 equiv aryl chloride, 1.2 equiv amine, and 1.4 equiv K2CO3.

[b]

Yields represent isolated yields (average of 2 runs).

[c]

Reaction time of 2 h.

[d]

2.5 equiv of K2CO3 was used.