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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 2.

C-H functionalization/triethylsilylation of substituted indoles.[a]

Entry Indole Adduct Yield [%]
1 graphic file with name nihms379119t1.jpg
3 		graphic file with name nihms379119t2.jpg
4 		90
2 graphic file with name nihms379119t3.jpg
5 		graphic file with name nihms379119t4.jpg
6 		82
3 graphic file with name nihms379119t5.jpg
7 		graphic file with name nihms379119t6.jpg
8 		86
4 graphic file with name nihms379119t7.jpg
9 		graphic file with name nihms379119t8.jpg
10 		55[b]
5 graphic file with name nihms379119t9.jpg
11 		graphic file with name nihms379119t10.jpg
12 		76
6 graphic file with name nihms379119t11.jpg
13 		graphic file with name nihms379119t12.jpg
14 		64
7 graphic file with name nihms379119t13.jpg
15 		graphic file with name nihms379119t14.jpg
16 		52[b]
8 graphic file with name nihms379119t15.jpg
17 		graphic file with name nihms379119t16.jpg
18 		41[b]
9 graphic file with name nihms379119t17.jpg
19 		graphic file with name nihms379119t18.jpg
20 		49
10 graphic file with name nihms379119t19.jpg
21 		graphic file with name nihms379119t20.jpg
22 		70
[a]

Reaction conditions: 5 mol% [Ir(OMe)(COD)]2, 10 mol% 4,4-di-tert- butyl-2,2-bipyridine (dtbpy), Et3SiH (3 equiv), and norbornene (3 equiv) in THF at 80°C for 24 h.

[b]

Same as [a], except 10 mol% [Ir(OMe)(COD)]2 and 20 mol% dtbpy for 36–48 h.