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. Author manuscript; available in PMC: 2013 Jun 19.
Published in final edited form as: J Am Chem Soc. 2008 Jan 4;130(4):1440–1452. doi: 10.1021/ja0773507

Table 7.

Optimization of Reaction Conditions for Cycloisomerization of 25

graphic file with name nihms382578u7.jpg

entry cat mol % solvent T, °C yield (%)a
1 AuBr3 5 tolueneb 100 23
2 AuI 5 tolueneb 100 traces
3 Au(PPh3)OTf 1 tolueneb 100 100 (89)
4 Au(PPh3)OTf 5 DCMc rt 99
5 PtCl2 5 toluened 100 21
6 PtCl4 5 toluened 100 21
7 Pd(PhCN)2Cl2 5 toluened 100 35
8 CuX (X = Cl, Br, I) 5 toluened 100 0
9 [CuOTf]2•PhH 5 toluened 100 42
10 Cu(OTf)2 5 toluenee 100 95
11 AgPF6 5 toluenee 100 47
12 AgOTf 5 toluenee 100 (80)
13 AgOTf 20 DCMc rt 70 (62)
14 Al(OTf)3 5 toluenee 100 64
15 Zn(OTf)2 5 toluenee 100 39
16 TMSOTf 20 DCMd rt 82 (62)
17 In(OTf)3 5 toluenee 100 91 (81)
18 Sn(OTf)2 5 toluenee 100 97 (81)
19 TIPSOTf 5 toluenee 100 100 (81)
20 TMSNTf2 5 toluenee 100 72
a

aNMR yield, isolated yield in parentheses (entries 1–4: Ar = p-Br–C6H4; entries 5–20: Ar = Ph).

b

Solution (0.05 M) of 25.

c

Solution (0.02 M) of 25.

d

Solution (1 M) of 25.

e

Solution (0.1 M) of 25.