Table 5.
entry | carboxylic acid | silylaryl triflate (equiv) |
CsF (equiv) |
time (h) |
product | % isolated yield |
---|---|---|---|---|---|---|
1 | 1a (2.0) | 4.0 | 24 | 81 | ||
2 | 1a (2.0) | 4.0 | 24 | 66 | ||
4 | 1a (2.0) | 4.0 | 24 | 96 | ||
5 | 1b (2.0) | 4.0 | 24 | 98 | ||
6 | 1a (2.0) | 4.0 | 24 | 84 | ||
7 | 1c (2.0) | 4.0 | 24 | 81 | ||
8 | 1a (2.0) | 4.0 | 24 | 75 | ||
9 | 1a (2.0) | 4.0 | 24 | 89 | ||
10 | 1b (2.0) | 4.0 | 24 | 89 | ||
11 | 1a (2.0) | 4.0 | 24 | 45 | ||
12 | 1a (2.0) | 4.0 | 24 | 33 |
All reactions were run under the following reaction conditions, unless otherwise specified: 0.25 mmol of the carboxylic acid and the indicated amount of silylaryl triflate and CsF were stirred in 4 mL of MeCN at room temperature.