Table 1.
Reaction parameters for C-H functionalization of indole 1 to 2.[a]
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---|---|---|---|---|
Entry | Et3SiH (equiv) | Co-Reactant (equiv) | Solvent | Yield [%] |
1 | 5 | none | Octane | 0[b] |
2 | 5 | none | THF | 4 |
3 | 5 | Cyclopentene (5) | THF | 15 |
4 | 5 | 2-norbornene (5) | THF | 85 |
5 | 5 | 2-norbornene (5) | Octane | 22 |
6 | 5 | 2-norbornene (5) | DME | 49 |
7 | 5 | 2-norbornene (5) | dioxane | 59 |
8 | 3 | 2-norbornene (3) | THF | 87 |
9 | 1.5 | 2-norbornene (1.5) | THF | 15 |
10 | 3 | 2-norbornene (0.5) | THF | 7 |
11 | 1.5 | 2-norbornene (3) | THF | 43 |
Reaction conditions: 5 mol% [Ir(OMe)(COD)]2 and 10 mol% 4,4-di-tert- butyl-2,2-bipyridine (dtbpy) at 80°C for 24 h.
At 120°C for 24 h.