Table 1.
Evaluation of Reaction Conditions for the Direct Arylation of 1-Fluoronaphthalene (1a)
| ||
|---|---|---|
| entry | deviation on reaction conditions | yield (%)a |
| 1 | none | 81 |
| 2 | Cy3P, instead of tBuPCy2 | 50 |
| 3 | Cy2PPh, instead of tBuPCy2 | 41 |
| 4 | tBu3P, instead of tBuPCy2 | 35 |
| 5 | Ph3P, instead of tBuPCy2 | 10 |
| 6 | (o-Tolyl)3P, instead of tBuPCy2 | <5 |
| 7 | AgOAc (1 equiv), instead of Ag2O | 38 |
| 8 | Ag2CO3, instead of Ag2O | 43 |
| 9 | AgNO3, instead of Ag2O | 56 |
| 10 | K2CO3, instead of Cs2CO3 | 24 |
| 11 | Na2CO3, instead of Cs2CO3 | 20 |
| 12 | without Pd(OAc)2 | <5 |
| 13 | without tBuPCy2 | <5 |
| 14 | without Ag2O | <5 |
Determined by 19F NMR in CDCl3 with C6H5F as internal standard.