Table 2.
Control Experiments Establishing an Acid-Catalyzed Mechanism for the Rearrangement of Furan 5b to Indole 6
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entry | modificationa | time | NMR yield of 6(%)b |
1 | none | 6 h | 86 |
2 | hν = 350 nm | 5 min | 84 |
3 | no light | 6 h | trace |
4 | 0.5 equiv of K2CO3 | 6 h | trace |
5 | no light, 3 mol % of Rh2(esp)2 | 6 h | 27 |
6 | no light, 10 mol % of TsOH | 1 h | 89 |
No light = protected from light with aluminum foil.
Yields determined by 1H NMR (400 MHz) using bibenzyl as an internal standard.