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. Author manuscript; available in PMC: 2012 May 15.
Published in final edited form as: J Am Chem Soc. 2010 Nov 15;132(48):17108–17110. doi: 10.1021/ja108949w

Table 1.

Cross-Coupling of β-Trifluoroboratoamides with Aryl Halidesa

graphic file with name nihms252868t1.jpg

entry electrophile X product % isolated yield
1 graphic file with name nihms252868t2.jpg Cl graphic file with name nihms252868t3.jpg 90
Br 63
2 graphic file with name nihms252868t4.jpg Cl graphic file with name nihms252868t5.jpg 72
Br 74b
3 graphic file with name nihms252868t6.jpg Cl graphic file with name nihms252868t7.jpg o = 88
p = 91
5 graphic file with name nihms252868t8.jpg Cl graphic file with name nihms252868t9.jpg 81
6 graphic file with name nihms252868t10.jpg Cl graphic file with name nihms252868t11.jpg 76
Br 72b
7 graphic file with name nihms252868t12.jpg Cl graphic file with name nihms252868t13.jpg 66b
Br 47b
8 graphic file with name nihms252868t14.jpg Cl graphic file with name nihms252868t15.jpg 72
9 graphic file with name nihms252868t16.jpg Br graphic file with name nihms252868t17.jpg 92
10 graphic file with name nihms252868t18.jpg Cl graphic file with name nihms252868t19.jpg 83
11 graphic file with name nihms252868t20.jpg Cl graphic file with name nihms252868t21.jpg 80b
12 graphic file with name nihms252868t22.jpg Cl graphic file with name nihms252868t23.jpg 92b
13 graphic file with name nihms252868t24.jpg Cl graphic file with name nihms252868t25.jpg 71b
a

General Conditions: Pd(OAc)2 (10 mol %), XPhos9a (20 mol %), RBF3K (1 equiv), K2CO3 (3 equiv) and 6.7:1 CPME/H2O (0.25 M).

b

Reactions perform better with SPhos9b (20 mol %) and Cs2CO3 (3 equiv).