Table 1.

Cross-Coupling of Secondary Potassium Alkyltrifluoroborates with Aryl Halides^a

entry	product	% isolated yield	entry	product	% isolated yield
1		R=c-C5H9; X=CI; 87 R=c-C6H11; X=CI; 79b R=c-C5H9; X=Br; 83 R=c-C5H9; X=I; 70c R=i-Pr; X=CI; 78d	9		R=c-C5H9; X=CI; 82
2		R=c-C5H9; X=CI; 88 R=i-Pr; X=CI; 77e	10		R=c-C5H9; X=CI; 94
3		R=c-C5H9; X=CI; 51 R=c-C5H9; X=Br; 49	11		R=c-C5H9; X=CI; 57 R=c-C6H11; X=CI; 87b
4		R=c-C5H9; X=CI; 92 R=c-C5H9; X=Br; 81	12		R=c-C5H9; X=CI; 88
5		R=c-C5H9; X=CI; 89 R=c-C5H9; X=Br; 93	13		R=c-C5H9; X=CI, 92
6		R=c-C5H9; X=CI; 82 R=c-C5H9; X=Br; 77	14		R=c-C5H9; X=CI; 77
7		R=c-C5H9; X=CI; 89 R=c-C5H9; X=Br; 86	15		R=c-C5H9; X=Br; 72
8		R=c-C5H9; X=CI; NR R=c-C5H9; X=Br; NR

^aGeneral conditions: Pd(OAc)₂ (2 mol %), n-BuPAd₂ (3 mol %), RBF₃K (1.1 equiv), Cs₂CO₃ (3 equiv), and 10:1 toluene/H₂O (0.20 M), 100 °C, 24 h.

^bPd(OAc)₂ (5 mol %), n-BuPAd₂ (7.5 mol %), RBF₃K (1.3 equiv), 100 °C, 72 h.

^cGeneral conditions, 72 h.

^d~1:6 ratio of i-Pr to n-Pr.

^e3.5:1 ratio of i-Prton-Pr.