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. 2016 May 16;7(8):5530–5536. doi: 10.1039/c6sc00932h

Table 1. Gold-catalyzed synthesis of 8a: selected optimization a .

Inline graphic
Entry Acid Time Yield b
1 2.1 equiv. MsOH 24 h 47% c
2 1.3 equiv. MsOH, 1.1 equiv. TFA 20 h 63%
3 1.3 equiv. MsOH, 1.1 equiv. TFA 6 h 69% d
4 1.3 equiv. MsOH, 1.1 equiv. TFA 8 h 51% e
5 1.3 equiv. MsOH, 1.1 equiv. TFA 8 h 74% f

a[10a] = 0.1 M (0.12 mmol).

bIsolated yield after flash chromatography.

c39% starting material 10a was recovered.

d200 mg scale reaction, 3% AgOTf was added as an additive.

e1 g scale reaction, 5% PPh3AuNTf2, 2% AgOTf as an additive.

f3 g scale reaction, 5% PPh3AuNTf2, 2% AgOTf as an additive, 1 equiv. AgOTf was added with NaHCO3 (s, aq.) to facilitate the cyclization.