Table 3.
Survey of Oxidative Hydrolysis Conditions for Hydrosilane 37.
 | ||||||||
|---|---|---|---|---|---|---|---|---|
| yield, %g |
||||||||
| entrya | catalyst, mol % |
solvent | time, h | 37 | 38 | 39 | 40 | 36 |
| 1b | 4 | CH3CN | 4 | - | 73 | - | - | - |
| 2c | 4 | CH3CN | 1 | - | 70 | - | - | - |
| 3d | 8 | CH3CN | 2 | - | 47 | - | - | - |
| 4e,f | 3 | CH3CN | 3 | 19 | 52 | 3 | 23 | - |
| 5 | 8 | n-BuCN | 2 | - | 87 | 2 | - | - |
| 6 | 3 | n-BuCN | 4 | - | 84 | 4 | - | - |
| 7 | 3 | THF | 4 | - | 54 | 5 | - | 27 |
| 8 | 4 | PhCN | 4 | - | 90 | 4 | - | - |
| C6H6/ | ||||||||
| 9 | 3 | CH3CN | 1 | - | 86 | 7 | - | - |
| (1:1) | ||||||||
| C6H6/ | ||||||||
| 10h | 3 | CH3CN | 1 | - | 84 | 8 | - | - |
| (1:1) | ||||||||
a
All the reactions were carried out on 100 mg scale, unless otherwise stated.
b
110 mg scale
c
564 mg scale.
d
950 mg scale.
e
[Ir(cod)Cl]2, H2O (2.0 equiv) were used.
f
TES ether cleavage was observed.
g
Yield of isolated product.
h
The reaction was run on 1.6 mmol scale and the yield of 38 is of analytically pure material.