Table 1.
Evaluation of monophosphite ligands L1–L4 in Rh-catalysed hydroformylation of styrene a.
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Entry | Ligand (L) | P (bar) | T (°C) | Conversion (%) | Regio. (iso/n ratio) |
1 | - | 10 | 80 | 96 | 50/50 |
2 | L3-(S)-BINOL-(−)-menthol | 10 | 80 | 99 | 61/39 |
3 | L4-(R)-BINOL-(+)-menthol | 10 | 80 | 99 | 59/41 |
4 | L4-(R)-BINOL-(+)-menthol | 20 | 80 | 99 | 65/35 |
5 | L4-(R)-BINOL-(+)-menthol | 25 | 80 | 99 | 64/36 |
6 | L4-(R)-BINOL-(+)-menthol | 20 | 50 | 92 | 94/6 |
7 | L4-(R)-BINOL-(+)-menthol | 25 | 50 | 95 | 96/4 |
8 | L1-(S)-BINOL-(+)-menthol | 25 | 50 | 93 | 96/4 |
9 | L2-(R)-BINOL-(−)-menthol | 25 | 50 | 94 | 96/4 |
a Reaction conditions: 2.32 mmol styrene; 0.006 mmol Rh(CO)2(acac), 0.03 mmol phosphite ligand; styrene/Rh = 400, P/Rh = 5, t = 4 h; Chemoselectivity for aldehydes was ≥ 99% in all cases.