Screening of reaction conditionsa.
| ||||
|---|---|---|---|---|
| Entry | Mediator | Solvent | T (°C) | Yieldc (%) |
| 1 | MnCl2 | CHCl3 : EtOH | 30 | 56(37), NDe |
| 2 | MnCl2 | CHCl3 : EtOH | 60 | 51(40) |
| 3 | MnCl2 | CHCl3 : EtOH | 80 | 52(40) |
| 4 | MnBr2 | CHCl3 : EtOH | 30 | 54(42) |
| 5 | MnI2 | CHCl3 : EtOH | 30 | Trace |
| 6 | MnCO3 | CHCl3 : EtOH | 80 | NDd |
| 7 | Mn(OTf)2 | CHCl3 : EtOH | 80 | NDd |
| 8 | Mn(acac)3 | CHCl3 : EtOH | 80 | NDd |
| 9 | Mn(OAc)3 | CHCl3 : EtOH | 80 | NDd |
| 10 | FeCl3 | CHCl3 : EtOH | 80 | NDd |
| 11 | CoCl2 | CHCl3 : EtOH | 80 | NDd |
| 12 | NiCl2 | CHCl3 : EtOH | 80 | NDd |
| 13 | CuCl2 | CHCl3 : EtOH | 80 | NDd |
| 14 | MnCl2 | Toluene | 80 | Trace |
| 15 | MnCl2 | Chloroform | 80 | 38(35) |
| 16 | MnCl2 | Ethanol | 80 | <5(11) |
| 17 | MnCl2 | THF | 80 | 42(47) |
| 18 | MnCl2 | Acetonitrile | 80 | 29(34) |
| 19 | MnCl2b | CHCl3 : EtOH | 30 | Trace |
Reaction conditions: BINAP (0.16 mmol), metal-mediator (3.0 eq.). aMixed-solvent (Vchloroform : VEtOH = 2 : 1, 10 mL), under an O2 atmosphere (1 bar) at corresponding temperature for 5–10 minutes.
10 mol%.
Isolated yields for helicenes and BINAPOs (in parentheses).
ND represents not detected.
Ar instead of O2.