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. 2014 Nov 20;5(1):167–175. doi: 10.1021/cs501813v

Table 1. Reaction Development for the Palladium-Catalyzed C8 Arylation of Quinoline N-Oxidesa.

graphic file with name cs-2014-01813v_0002.jpg

        yield (%)
 
entry catalyst (5 mol %) AgX (amt (equiv)) additive (amt (equiv)) 1 2 (C8) 3 (C2) C8/C2 (2/3)
1 Pd(OAc)2   AcOH (10) 91 8 0.6 12:1
2 Pd(OAc)2 AgOAc (3) AcOH (10) 38 39 3 13:1
3 Pd(OAc)2 AgOAc (3) DMF (10) 29 5 36 1:7
4 Pd(OAc)2 AgOAc (3) tBuOH (10) 50 7 41 1:6
5 PdCl2 AgOAc (3) AcOH (10) 7 17 2 9:1
6 Pd(TFA)2 AgOAc (3) AcOH (10) 27 40 11 4:1
7 Pd(OAc)2 Ag2CO3 (0.5) AcOH (10) 29 23 3 8:1
8 Pd(OAc)2 Ag3PO4 (0.5) AcOH (10) <2 73 <2 >30:1
9 Pd(OAc)2 Ag3PO4 (0.5) AcOH (30) 8 78 <2 >30:1
10 Pd(OAc)2 Ag3PO4(0.5) AcOH (30)/H2O (5.5) 1 95 4 23:1
11b Pd(OAc)2 Ag3PO4(0.5) AcOH (30)/H2O (5.5) 6 90 3 30:1
12c Pd(OAc)2 Ag3PO4(0.5) AcOH (30)/H2O (40) 28 65 <2 >30:1
a

Yields were determined by 1H NMR analysis with 1,4-dimethoxybenzene as an internal standard added prior to workup. Reaction conditions: 1 (0.2 mmol), 4 (3 equiv), with the catalyst and the additives under Ar for 12 h at 120 °C.

b

Reaction was run under microwave irradiation at 180 °C for 45 min.

c

Reaction was run under microwave irradiation at 180 °C for 10 min.