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. 2011 Sep 9;76(21):8781–8793. doi: 10.1021/jo201511d

Table 3. Copper-Catalyzed Indolation of THIQ.

graphic file with name jo-2011-01511d_0008.jpg

entry R X amt of THIQ (equiv) yield (%)
1 (5h) H CH 8.0 84
2 (5h) H CH 4.0 85
3 (5h) H CH 2.0 74
4 (5h) H CH 0.8 48
5 (5h) H CH 0.4 53
6 (5i) 1-Me CH 0.8 1
7 (5j) 2-Me CH 0.8 43
8 3-Me CH 0.8 ncb
9 (5l) 5-OMe CH 0.8 48
10 (5l) 5-OMe CH 2.0 71
11 (5m) 5-NO2 CH 0.8 53a
12 (5m) 5-NO2 CH 2.0 62a
13 (5n) 5-COOMe CH 2.0 58
14 (5p) 6-Cl CH 0.8 46
15 (5q) 7-NO2 CH 0.8 2
16 (5r)   N 0.8 43
17 (5t) 7-Me CH 0.8 48
18 (5t) 7-Me CH 2.0 68
a

Reaction time: 2 days.

b

nc = no conversion.