Table 3. Treatment of CuI, NaBPh4, and Different Ligands with CO2 in MeOHa.
| entry | CuI [μmol] | ligand | t [h] | 13C NMR (C2O42–) | CE (C2O42– (?)) [%]b |
|---|---|---|---|---|---|
| 1 | 123 | L2 | 120 | n.d. | <0.5 |
| 2 | 124 | L3 | 120 | n.d. | <0.5 |
| 3 | 151 | dpa | 120 | n.d. | 2 |
| 4 | 184 | dien | 119 | n.d. | 28 |
| 5 | 409 | dien | 119 | n.d. | 10 |
| 6c | 180 | dien | 120 | n.d. | 26 |
| 7 | 53 | L4 | 114 | n.d. | 5 |
| 8d | 63 | L4 | 118 | n.d. | 29 |
| 9d | 187 | L4 | 119 | n.d. | 19 |
| 10d,e | 187 | L4 | 119 | n.d. | 28 |
| 11d,f | 94 | L4 | 118 | n.d. | 32 |
| 12c,d | 63 | L4 | 124 | n.d. | 3 |
| 13c,d | 94 | L4 | 118 | n.d. | <0.5 |
Reaction conditions: CuI/ligand/NaBPh4 (1:1:1) was utilized in degassed MeOH under constant CO2 atmosphere, unless stated otherwise. n.d. = not detected.
Oxalate yields were calculated for signals coinciding with Na2C2O4 added as internal standard after initial measurement and were found to overlap with the signal of iodide.
Reaction conducted under Ar.
A total of 0.5 equiv of L4 was utilized.
Reaction conducted with 13CO2.
Reaction conducted without NaBPh4.
