Table 1. Optimization of the cross-coupling reaction involving double deamination.
Reaction condition: 1 (0.3 mmol), 2 (0.9 mmol), [Ni] (0.045 mmol), ligand (0.045 mmol), NaI (0.5 M), DMA (3 ml), Ar atmosphere, and rt. Detected by gas chromatography with dodecane as the internal standard. NFE, nickel foam electrode; n.d., not detected.
Entry | Variation from the standard conditions | Yield [%] |
---|---|---|
1 | None | 74 (70)* |
2 | (+)C/(−)NFE, 2.5 equiv of B2pin2 or Et3N | n.d. |
3 | TBAB or TBAI or NaBr | 33–62 |
4 | 2.5 mA/12 h | 54 |
5 | 10 mA/3 h | 65 |
6 | No electricity | n.d. |
7 | W/o NiBr2 dme | Trace |
*Isolated yield.