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. Author manuscript; available in PMC: 2011 Dec 17.
Published in final edited form as: Org Lett. 2010 Nov 19;12(24):5783–5785. doi: 10.1021/ol102717x

Table 2.

Cross-Coupling of 2-(Bromomethyl)tetrahydro-2H-pyran with Potassium Heteroaryltrifluoroborates

graphic file with name nihms254080u3.jpg
entry R-BF3K yield % entry R-BF3K yield %
1 graphic file with name nihms254080t10.jpg X = O, 71
X = S, 63		 7 graphic file with name nihms254080t11.jpg 78
2 graphic file with name nihms254080t12.jpg 66 8 graphic file with name nihms254080t13.jpg 82
3 graphic file with name nihms254080t14.jpg 35 9 graphic file with name nihms254080t15.jpg 70
4 graphic file with name nihms254080t16.jpg X = O, 68
X = S, 81(74)a 		10 graphic file with name nihms254080t17.jpg 71
11 graphic file with name nihms254080t18.jpg 59
5 graphic file with name nihms254080t19.jpg X = O, 80
X = S, 58		 12 graphic file with name nihms254080t20.jpg 51
6 graphic file with name nihms254080t21.jpg R = H, 77
R = OMe, 71		 13 graphic file with name nihms254080t22.jpg 63
a

Reaction performed on 5 mmol scale using 1 mol % catalyst loading.