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. Author manuscript; available in PMC: 2022 Jun 6.
Published in final edited form as: Org Lett. 2019 Mar 22;21(7):2397–2401. doi: 10.1021/acs.orglett.9b00682

Table 2.

Control Experiments Establishing an Acid-Catalyzed Mechanism for the Rearrangement of Furan 5b to Indole 6

graphic file with name nihms-1704817-t0003.jpg
entry modificationa time NMR yield of 6(%)b
1 none 6 h 86
2 = 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
a

No light = protected from light with aluminum foil.

b

Yields determined by 1H NMR (400 MHz) using bibenzyl as an internal standard.