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. Author manuscript; available in PMC: 2010 Nov 25.
Published in final edited form as: J Am Chem Soc. 2009 Nov 25;131(46):16720–16734. doi: 10.1021/ja9044357

Table 2.

Pd-Catalyzed Coupling of Aryl Nonaflates and Triflates with Secondary Ureas, Carbamates, and Sulfonamides.a

graphic file with name nihms157145u2.jpg
entry ArX amide product yieldb
1 graphic file with name nihms157145t28.jpg graphic file with name nihms157145t29.jpg graphic file with name nihms157145t30.jpg 64%
2 graphic file with name nihms157145t31.jpg graphic file with name nihms157145t32.jpg graphic file with name nihms157145t33.jpg 53%
3 graphic file with name nihms157145t34.jpg graphic file with name nihms157145t35.jpg graphic file with name nihms157145t36.jpg 90%
4 graphic file with name nihms157145t37.jpg graphic file with name nihms157145t38.jpg graphic file with name nihms157145t39.jpg 88%
5 graphic file with name nihms157145t40.jpg graphic file with name nihms157145t41.jpg graphic file with name nihms157145t42.jpg 86%
6 graphic file with name nihms157145t43.jpg graphic file with name nihms157145t44.jpg graphic file with name nihms157145t45.jpg 87%
7 graphic file with name nihms157145t46.jpg graphic file with name nihms157145t47.jpg graphic file with name nihms157145t48.jpg 88%
8 graphic file with name nihms157145t49.jpg graphic file with name nihms157145t50.jpg graphic file with name nihms157145t51.jpg 83%
9 graphic file with name nihms157145t52.jpg graphic file with name nihms157145t53.jpg graphic file with name nihms157145t54.jpg 87%
10 graphic file with name nihms157145t55.jpg graphic file with name nihms157145t56.jpg graphic file with name nihms157145t57.jpg 77%
a

Reaction conditions: ArONf/ArOTf (1 equiv), urea or carbamate (2.5 equiv), [(allyl)PdCl]2 (1 mol%), JackiePhos (5 mol%), K2CO3 (2.0 equiv), 3 Å mol sieves (50 mg/ml), toluene (0.25 M), 110 °C, 17 h.

b

Yields reported are an average of at least two runs determined to be >95% pure by elemental analysis or 1H NMR.