Table 1.
Optimization of ortho-Acetoxylation Reaction Conditions

| entry | substrate | additive (equiv) | solvent | T, °C | yield, %a |
|---|---|---|---|---|---|
| 1 | A | none | PrCN | 80 | -b |
| 2 | B | none | PrCN | 80 | -b |
| 3 | 1a | none | PrCN | 80 | 15 (2a)b |
| 4 | 1a | none | PrCN | 100 | 30 (2a)b |
| 5 | 1a | Cu(OAc)2 (1) | PrCN | 100 | trace (2a) |
| 6 | 1a | AgOAc (1) | PrCN | 80 | 70 (2a) |
| 7 | 1a | AgOAc (1) | PrCN | 100 | 80 (2a) |
| 8 | 1a | AgOAc (1) | DCE | 80 | 85 (2a) |
NMR yield.
Decomposition of starting arylsilane was observed.