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. Author manuscript; available in PMC: 2010 Oct 1.
Published in final edited form as: Org Lett. 2009 Oct 1;11(19):4330–4333. doi: 10.1021/ol901669k

Table 3.

One-Pot Preparation of Potassium Azidoaryltrifluoroboratesa

graphic file with name nihms-144872-f0039.jpg
entry X–Ar–BF3K reaction time (h) product yield
1 graphic file with name nihms-144872-t0040.jpg 1a-Br
1a-I
7
1
graphic file with name nihms-144872-t0041.jpg 1b 95%
95%b
2 graphic file with name nihms-144872-t0042.jpg 2a-Br
2a-I
9
6
graphic file with name nihms-144872-t0043.jpg 2b 90%
93%
3 graphic file with name nihms-144872-t0044.jpg 3a 24 graphic file with name nihms-144872-t0045.jpg 3b 73%
4 graphic file with name nihms-144872-t0046.jpg 4a 8 graphic file with name nihms-144872-t0047.jpg 4b 93%
5 graphic file with name nihms-144872-t0048.jpg 5a 12 graphic file with name nihms-144872-t0049.jpg 5b 90%
6 graphic file with name nihms-144872-t0050.jpg 6a 4 graphic file with name nihms-144872-t0051.jpg 6b 92%c
7 graphic file with name nihms-144872-t0052.jpg 7a 12 graphic file with name nihms-144872-t0053.jpg 7b 83%c
8 graphic file with name nihms-144872-t0054.jpg 8a 12 graphic file with name nihms-144872-t0055.jpg 8b 91%c
9 graphic file with name nihms-144872-t0056.jpg 9a 1 graphic file with name nihms-144872-t0057.jpg 9b 98%
10 graphic file with name nihms-144872-t0058.jpg 10a 1 graphic file with name nihms-144872-t0059.jpg 10b 98%
11 graphic file with name nihms-144872-t0060.jpg 11a 3 graphic file with name nihms-144872-t0061.jpg 11b 95%
12 graphic file with name nihms-144872-t0062.jpg 12a 3 graphic file with name nihms-144872-t0063.jpg 12b 95%
13 graphic file with name nihms-144872-t0064.jpg 13a 12 graphic file with name nihms-144872-t0065.jpg 13b 90%
14 graphic file with name nihms-144872-t0066.jpg 14a 10 graphic file with name nihms-144872-t0067.jpg 14b (82%)c,d
15 graphic file with name nihms-144872-t0068.jpg 15a 13 graphic file with name nihms-144872-t0069.jpg 15b (82%)e
16 graphic file with name nihms-144872-t0070.jpg 16a 5 min graphic file with name nihms-144872-t0071.jpg 16b 96%
a

All reactions were performed on a 1.0 mmol scale in 4 mL of DMSO and monitored by 1H NMR in D2O. Yields are given for isolated products.

b

Reaction was performed on a 3.0 mmol scale.

c

Products were obtained as amorphous solids.

d

Product was contaminated with about 10% of 14a.

e

Product was contaminated with about 15% of the azide product.