Table 1 Optimization of the reaction conditions.a
From: Atroposelective hydroarylation of biaryl phosphines directed by phosphorus centres
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|---|---|---|---|---|---|---|
Entry | Cat [M] (mol%) | L* (mol%) | Solvent | T (°C) | Ee of 3aa (%)b | Yield of 3aa (%)c |
1 | [Ir(cod)Cl]2 (5) | L1 (11) | Toluene | 70 | 0 | 33 |
2 | [Ir(cod)Cl]2 (5) | L2 (11) | Toluene | 70 | 51 | 79 |
3 | [Ir(cod)Cl]2 (5) | L3 (11) | Toluene | 70 | 97 | 82 |
4 | [Ir(cod)Cl]2 (5) | L4 (11) | Toluene | 70 | −66 | 76 |
5 | [Ir(cod)Cl]2 (5) | L5 (11) | Toluene | 70 | – | <5 |
6 | [Ir(cod)Cl]2 (5) | L3 (11) | THF | 70 | 71 | 44 |
7 | [Ir(cod)Cl]2 (5) | L3 (11) | DCM | 70 | 83 | 23 |
8 | [Ir(cod)Cl]2 (5) | L3 (11) | Toluene | 90 | 93 | 88 |
9 | [Ir(cod)Cl]2 (5) | L3 (11) | Toluene | rt | 99 | 11 |
10 | [Ir(coe)2Cl]2 (5) | L3 (11) | Toluene | 70 | 77 | 77 |
11 | [Rh(cod)Cl]2 (5) | L3 (11) | Toluene | 70 | 12 | 70 |
12 | Pd(OAc)2 (5) | L3 (11) | Toluene | 70 | – | 0 |
13 | [Ir(cod)Cl]2 (2.5) | L3 (5.5) | Toluene | 70 | 98 | 15 |
14 | – | L3 (11) | Toluene | 70 | – | 0 |
