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. Author manuscript; available in PMC: 2013 Sep 10.
Published in final edited form as: Angew Chem Int Ed Engl. 2008;47(39):7508–7510. doi: 10.1002/anie.200802456

Table 1.

Reaction parameters for C-H functionalization of indole 1 to 2.[a]

graphic file with name nihms379119u2.jpg
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
[a]

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.

[b]

At 120°C for 24 h.