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. 2013 Oct 2;9:2002–2008. doi: 10.3762/bjoc.9.235

Table 1.

Hydrophenoxylation of unactivated internal alkynes.a

graphic file with name Beilstein_J_Org_Chem-09-2002-i001.jpg

Entry Gold catalyst Conv.b
R = Ph Bu

1 None 0 0
2 (JohnPhos)AuCl 0 0
3 (t-BuXPhos)AuCl 0 0
4 (IMes)AuCl 0 0
5 (SIMes)AuCl 0 0
6 (IPr)AuCl 0 0
7 (SIPr)AuCl 0 0
8 1 98 95
9 2 62 48
10 2 + t-BuXPhos 79 60
11 3 77 70
12 4 47 50
13 5 63 48
14 6 64 45
15 7 86 92
16 8 89 95
17 9 90 91
18 1 Conventional heating 95 93

aDiphenylacetylene or 5-decyne (0.28 mmol), 4-nitrophenol (0.56 mmol), catalyst (14.0 μmol, 5%), 130 °C, 20 min, no solvent, microwave irradiation. bBased upon 1H NMR spectroscopy using anisole as an internal standard.