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. 2017 Nov 30;2(11):8507–8516. doi: 10.1021/acsomega.7b01637

Table 1. Optimization of Reaction Conditionsa.

graphic file with name ao-2017-01637b_0006.jpg

entry catalyst additive solvent temp (°C) yield (%)b
1 Rh(PPh3)3Cl AgNTf2 DCE reflux trace
2 Rh2(OAc)4 AgNTf2 DCE reflux trace
3 [Cp*Co(CO)I2] AgNTf2 DCE reflux trace
4 [Cp*RhCl2]2 AgNTf2 DCE reflux 81
5   AgNTf2 DCE reflux trace
6 [Cp*RhCl2]2 AgNTf2 MeOH reflux 31
7 [Cp*RhCl2]2 AgNTf2 EtOH reflux 35
8 [Cp*RhCl2]2 AgNTf2 toluene 100 56
9 [Cp*RhCl2]2 AgNTf2 DCM reflux 51
10 [Cp*RhCl2]2 AgNTf2 TFEA reflux 28
11c [Cp*RhCl2]2 AgNTf2 DCE reflux 49
12d [Cp*RhCl2]2 AgNTf2 DCE reflux 75
13e [Cp*RhCl2]2 AgNTf2 DCE reflux 46
14f [Cp*RhCl2]2 AgNTf2 DCE reflux 78
15 [Cp*RhCl2]2 AgNTf2 DCE rt trace
16 [Cp*RhCl2]2 AgNTf2 DCE 40 18
17 [Cp*RhCl2]2 AgNTf2 DCE 60 32
18 [Cp*RhCl2]2 AgNTf2 DCE 80 65
a

Reaction conditions: 2-diazo-5,5-dimethylcyclohexane-1,3-dione 1e (0.5 mmol), acetanilide 2a (0.5 mmol), solvent (3 mL), and catalyst (1.0 mol %) for 12 h.

b

Isolated yields.

c

5 mol % of additive was used.

d

20 mol % of additive was used.

e

0.5 mol % of catalyst was used.

f

2 mol % of catalyst was used.