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. 2022 May 19;12(11):6596–6605. doi: 10.1021/acscatal.2c00710

Table 1. Optimization Studies for the Acetoxylation of Substrate 1a.

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entry catalyst Z-2a/3aa yield (%)b
1 Pd(OAc)2 >98:2 86
2 Pt(CH3CN)2Cl2 44:56 72
3 AuCl(PPh3)/AgOTf 62:38 66
4 AgSbF6 decomp  
5 Zn(ClO4)2·6H2O nr  
6c Pd(OAc)2 >98:2 41
7d Pd(OAc)2 >98:2 76
8 PdBr2 nr  
9 Pd(acac)2 >98:2 10
10 Pd(TFA)2 nr  
11 PdCl2(CH3CN)2 decomp  
12 none nr  
13 Pd/Aue 94:6 79
14 Pd(OAc)2,H2Of 86:14 81
15 Pd/Aue,H2Of 52:48 85
a

Determined by 1H NMR spectroscopy from the crude mixture.

b

Determined by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard.

c

3 mol % Pd(OAc)2 was used.

d

Reaction performed at 60 °C during 5 h for full completion.

e

A combination of Pd(OAc)2 (5 mol %) and AuCl(PPh3)/AgOTf (5 mol %) was used as a catalyst.

f

Extra water (10% v/v) was added to the reaction mixture. nr: no reaction (starting material recovered).