Table 1.
Entry | Oxidant | Result | Entry | Oxidant | Result |
---|---|---|---|---|---|
1 | None | 9% | 5 | Isoprene | 0 |
2b | Air | Trace | 6 | Ag2O | Trace |
3c | O2 | 0 | 7 | CuO | 15% |
4 | NCS | 0 | 8 | DCB | 21% |
aReaction conditions: 1a (0.25 mmol), 2a (0.2 mmol), Ru(PPh3)3Cl2 (3 mol %), dcypf (3 mol %), K3PO4 (1.1 equiv), oxidant (2.0 equiv), solvent (0.2 mL) at 70 °C under N2 atmosphere. See Supplementary Information (SI) for details. 1H NMR yield was determined using mesitylene as an internal standard. A ‘trace’ amount of product was noted when the desired product was not clearly detected.
bThe reaction was performed under air.
cOxygen balloon was used to provide O2 gas during the reaction.