Table 3.
| ||||||
---|---|---|---|---|---|---|
entry | X–Ar–BF3K | reaction time (h) | product | yield | ||
1 |
1a-Br 1a-I |
7 1 |
1b | 95% 95%b |
||
2 |
2a-Br 2a-I |
9 6 |
2b | 90% 93% |
||
3 | 3a | 24 | 3b | 73% | ||
4 | 4a | 8 | 4b | 93% | ||
5 | 5a | 12 | 5b | 90% | ||
6 | 6a | 4 | 6b | 92%c | ||
7 | 7a | 12 | 7b | 83%c | ||
8 | 8a | 12 | 8b | 91%c | ||
9 | 9a | 1 | 9b | 98% | ||
10 | 10a | 1 | 10b | 98% | ||
11 | 11a | 3 | 11b | 95% | ||
12 | 12a | 3 | 12b | 95% | ||
13 | 13a | 12 | 13b | 90% | ||
14 | 14a | 10 | 14b | (82%)c,d | ||
15 | 15a | 13 | 15b | (82%)e | ||
16 | 16a | 5 min | 16b | 96% |
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.
Reaction was performed on a 3.0 mmol scale.
Products were obtained as amorphous solids.
Product was contaminated with about 10% of 14a.
Product was contaminated with about 15% of the azide product.