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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 1.

Pd-Catalyzed Coupling of Aryl Nonaflates and Triflates with Secondary Amides.a

graphic file with name nihms157145u1.jpg
entry ArX amide product yieldb
graphic file with name nihms157145t1.jpg graphic file with name nihms157145t2.jpg graphic file with name nihms157145t3.jpg
1 R = t-Bu 1 R = t-Bu 79%
2 R = Me 2 R = Me 85%
3 R = CO2Me 3 R = CO2Me 87%
4 graphic file with name nihms157145t4.jpg graphic file with name nihms157145t5.jpg graphic file with name nihms157145t6.jpg 79%
5 graphic file with name nihms157145t7.jpg graphic file with name nihms157145t8.jpg graphic file with name nihms157145t9.jpg 85%
6c graphic file with name nihms157145t10.jpg graphic file with name nihms157145t11.jpg graphic file with name nihms157145t12.jpg 82%
7 graphic file with name nihms157145t13.jpg graphic file with name nihms157145t14.jpg graphic file with name nihms157145t15.jpg 76%
8 graphic file with name nihms157145t16.jpg graphic file with name nihms157145t17.jpg graphic file with name nihms157145t18.jpg 77%
9 graphic file with name nihms157145t19.jpg graphic file with name nihms157145t20.jpg graphic file with name nihms157145t21.jpg 72%
10 graphic file with name nihms157145t22.jpg graphic file with name nihms157145t23.jpg graphic file with name nihms157145t24.jpg 70%
11d graphic file with name nihms157145t25.jpg graphic file with name nihms157145t26.jpg graphic file with name nihms157145t27.jpg 78%
a

Reaction conditions: ArONf/ArOTf (1 equiv), amide (2.5 equiv), [(allyl)PdCl]2 (1 mol%), JackiePhos (5 mol%), K2CO3 (2.0 equiv), 3 Å mol sieves (200 mg/mmol), 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.

c

Pd(OAc)2 (3 mol%), JackiePhos (7 mol%), H2O activation

d

K3PO4 was used instead of K2CO3.