Table 4.
Evaluation of Xantphos Ligands in the Hydroamination of 1a.a
entry | % Rh | ligand | time (h) | %convb | ratiob2a:3a:4a:5a |
---|---|---|---|---|---|
1 | 1 | L1 | 2 | 100 | 18:1:1:0.7 |
2 | 1 | L1’ | 2 | 100 | 11:1:1:0.2 |
3 | 3 | L2 | 2 | 83 | 1:0.1:0:4.4 |
4 | 3 | L2’ | 2 | 62 | 1:0.2:0:9.1 |
5 | 3 | L3 | 2 | 47 | 2:1:1:0c |
6 | 3 | L4 | 2 | 100 | 5.7:1:1:0.4 |
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Reaction conditions: 0.2-0.3 mmol 1a, 1-3 mol % [Rh(CH3CN)2COD]BF4, and 1.2-3.5 mol % ligand in 0.4-0.6 mL of tBuOH at 70 °C.
Determined by 1H NMR spectroscopy.
Trace amount of isomerization observed.