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. Author manuscript; available in PMC: 2014 May 17.
Published in final edited form as: Org Lett. 2013 May 6;15(10):2534–2537. doi: 10.1021/ol401021x

Table 5.

Cross-Coupling of 1-Naphthol Sulfamate with Various Secondary Aminomethyltrifluoroborates 9a–f

graphic file with name nihms476824u6.jpg
entry product yield(%)b/conversion(%)c
1 graphic file with name nihms476824t36.jpg
10a, 71/100
2 graphic file with name nihms476824t37.jpg
10b, 68/100
3 graphic file with name nihms476824t38.jpg
10c, 0/0
4 graphic file with name nihms476824t39.jpg
10d, 74/89
5 graphic file with name nihms476824t40.jpg
10e, 82/97
6 graphic file with name nihms476824t41.jpg
10f, 86/100
a

Reaction conditions: 1.0 equiv of hetaryl sulfamate, 1.05 equiv of trifluoroborate, 4 mol % XPhos-Pd-G2, 7 equiv of K2CO3, t-BuOH/H2O (1:1, 0.5 M), 85 °C, 18 h.

b

isolated yield.

c

calculated by 1H NMR with 30 μL of CH2Cl2.