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. Author manuscript; available in PMC: 2021 Oct 1.
Published in final edited form as: Tetrahedron Lett. 2020 Aug 16;61(40):152333. doi: 10.1016/j.tetlet.2020.152333

Table 1.

Cycloisomerization of 12 under a variety of conditions.

Entry Conditionsa Time Conversionb
1 1, 24 °C 1 h 0%
1, 70 °C 1 h 0%
1, 70 °C 16 h 0%
2 AgOTf, 70 °C 1 h 0%
AgOTf, 70 °C 16 h 0%
3 1, + AgOTf, 24 °C 1 h 0%
1, + AgOTf, 70 °C 1 h 48%
1, + AgOTf, 70 °C 16 h 99%
4 2, 70 °C 1 h 0%
2, 70 °C 16 h 0%
5 2 + AgOTf, 24 °C 1 h 0%
2 + AgOTf, 70 °C 1 h 7%
2 + AgOTf, 70 °C 16 h 99%
6 AuCl, 70 °C 16 h 11%
7 AuCl, + AgOTf, 70 °C 16 h 8%c
a

[12] = 0.04 mM, [Au] = 0.002 mM (5 mol%), [additive] = 0.004 mM (10 mol%), reaction volume 0.60 mL.

b

As determined by NMR integration, all species were cleanly resolved and except for entry 7, the only observable compounds were starting 12 or product 24.

c

6% of fluorene 5 was detected.