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. Author manuscript; available in PMC: 2013 Jun 17.
Published in final edited form as: Angew Chem Int Ed Engl. 2007;46(27):5195–5197. doi: 10.1002/anie.200701128

Table 1.

Optimization of reaction conditions.a

graphic file with name nihms382574u1.jpg

Entry Catalystb mol% Solvent T [°C] Yield [%]c
1 AuBr3 5 toluened 100 23
2 AuI 5 toluened 100 traces
3 [Au(PPh3)]OTf 1 toluened 100 100 (89)
4 [Au(PPh3)]OTf 5 CH2Cl2e RT 99
5 PtCl2 5 toluenef 100 21
6 PtCl4 5 toluenef 100 21
7 [PdCl2(PhCN)2] 5 toluenef 100 35
8 CuX (X = Cl, Br, I) 5 toluenef 100 0
9 CuOTf·PhH 5 toluenef 100 42
10 Cu(OTf)2 5 tolueneg 100 95
11 AgPF6 5 tolueneg 100 47
12 AgOTf 5 tolueneg 100 (80)
13 AgOTf 20 CH2Cl2e RT 70 (62)
14 Al(OTf)3 5 tolueneg 100 64
15 Zn(OTf)2 5 tolueneg 100 39
16 TMSOTf 20 CH2Cl2e RT 82 (62)
17 In(OTf)3 5 tolueneg 100 91 (81)
18 Sn(OTf)2 5 tolueneg 100 97 (81)
19 TIPSOTf 5 tolueneg 100 100 (81)
20 TMSNTf2 5 tolueneg 100 72
a

Entries 1–4: Ar = p-Br-C6H4; entries 5–20: Ar = Ph.

b

Tf = trifluoromethanesulfonyl, TIPS = triisopropylsilyl, TMS = trimethylsilyl.

c

Yield determined from NMR spectrum; yield of isolated product in parentheses.

d

0.05 M, solution of 3.

e

0.02 M solution of 3.

f

1 M solution of 3.

g

0.1 M solution of 3.