Table 1.
| |||||
---|---|---|---|---|---|
entry | X–Ar–X | product | yield | ||
1 |
1a-Br 1a-I |
86% 90% |
|||
2 |
2a-Br 2a-I |
56% 85% |
|||
3 |
3a – |
52% – |
|||
4 | 4a | 81% | |||
5 | 5a | 47% | |||
6 | 6a | 82% | |||
7 | 7a | 82% | |||
8 | 8a | 72% | |||
9 | 9a | 90% | |||
10 | 10a | 87% | |||
11 | 11a | 90% | |||
12 | 12a | 85% | |||
13 | 13a | 93% | |||
14 | 14a | 94% | |||
15 | 15a | 90% | |||
16 | 16a | 80% |
Reaction conditions: aryl dihalide (2.0 mmol), triisopropyl borate (2.0 mmol), and n-BuLi (2.0 mmol) at −78 °C to rt under N2 and then quenched with 1 N KHF2.