Skip to main content
. 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 1.

Cross-Coupling of Various Aryl Sulfamates with Primary Aminomethyltrifluoroborate 1

graphic file with name nihms476824u2.jpg
entry product yield(%)b/conversion(%)c
1d graphic file with name nihms476824t1.jpg
2a, 93(93)h/100
2e graphic file with name nihms476824t2.jpg
2b, 85/90
3d graphic file with name nihms476824t3.jpg
2c,13b/27
4d graphic file with name nihms476824t4.jpg
2d, 38b/38
5d graphic file with name nihms476824t5.jpg
2e, 23b/25
6d graphic file with name nihms476824t6.jpg
2f, 90/100
7d graphic file with name nihms476824t7.jpg
2g, 88/100
8d graphic file with name nihms476824t8.jpg
2h, 93/100
9f graphic file with name nihms476824t9.jpg
2i, 72/75
89/98g
10d graphic file with name nihms476824t10.jpg
2j, 87/100
11e graphic file with name nihms476824t11.jpg
2k, 60/80
12e graphic file with name nihms476824t12.jpg
2l, 76/100
a

Reaction conditions: 1.0 equiv of aryl sulfamate, 1.05 equiv of trifluoroborate, 4 mol % XPhos-Pd-G2, K2CO3, t-BuOH/H2O (1:1, 0.5 M), 85 °C, 3 h.

b

isolated yield.

c

calculated by 1H NMR with 30 μL of CH2Cl2.

d

3 equiv K2CO3.

e

5 equiv K2CO3.

f

7 equiv K2CO3.

g

n-PrOH/H2O.

h

3 mmol of sulfamate, 2 mol % XPhos-Pd-G2, 3 equiv K2CO3, t-BuOH/H2O (1:1, 0.5 M), 85 °C, 18 h.