Catalyst and solvent screening for the manganese-catalyzed transfer hydrogenation of 1,3-diphenylurea (1a)a.
| |||||
|---|---|---|---|---|---|
| Entry | [Mn] | Co-solvent | 2a/% | 3a/% | 4a/% |
| 1 | Mn–I | — | 54 | 19 | 63 |
| 2 | Mn–II | — | 47 | 7 | 77 |
| 3 | Mn–III | — | 52 | — | 85 |
| 4 | Mn–IV | — | 71 | 45 | 54 |
| 5 | — | — | 46 | — | 90 |
| 6 | Mn–IV | CH2Cl2b | 39 | 5 | 35 |
| 7 | Mn–IV | THFb | 78 | 64 | 19 |
| 8 | Mn–IV | Tolueneb | 91 | 89 | — |
| 9 | Mn–IV | 1,4-Dioxaneb | 73 | 60 | 14 |
| 10c | Mn–IV | Tolueneb | 46 | 9 | 73 |
Reaction conditions: 1a (0.5 mmol), catalyst [Mn] (2 mol%), KOtBu (6 mol%), iPrOH (2 mL), 120 °C, 16 h. Yields were determined by GC using mesitylene as the internal standard.
iPrOH (1 mL) and cosolvent (1 mL).
100 °C.