Table 1 Optimization of the reaction conditionsa
From: Reverse polarity of amide nitrogen enables expedient access to N-cyano amides
| ||
|---|---|---|
Entry | Deviations from above | Yield |
1 | none | 94% (90%) |
2 | without CsF | 0% (rsm 95%) |
3 | KF instead of CsF | 48% |
4 | NaF instead of CsF | 0% (rsm 90%) |
5 | RbF instead of CsF | 86% |
6 | DMSO instead of MeCN | 36% |
7 | DMF instead of MeCN | 64% |
8 | THF instead of MeCN | trace (rsm 64%) |
9 | 25 °C | 73% |
10 | 60 °C | 33% (13%b) |
11 | 10 mmol scale | (83%, 1.33 g) |
12 | –OMs instead of –OTs | 71% |
13 | –ONos instead of –OTs | 33% |
14 | –OAc instead of –OTs | 0% |
15 | –OTf instead of –OTs | 0% |
16 | –OMe instead of –OTs | 0% |
