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. 2016 Sep 23;8(2):946–952. doi: 10.1039/c6sc03699f

Table 1. Au(i)-catalyzed C–O bond formation with different NaO–R a .

Inline graphic
Entry R–ONa Solvent Time (h) Product Yield b (%)
1 pCl-PhONa CH3CN 6 graphic file with name c6sc03699f-u2.jpg >99 c
2 HONa MeOH 8 graphic file with name c6sc03699f-u3.jpg >99
3 MeONa MeOH 8 >99 c
4 EtONa MeOH 24 >99
5 MeONa EtOH 24 86 (9) d
6 EtONa EtOH 24 graphic file with name c6sc03699f-u4.jpg 56 (78) e
7 (2-Propoxide)Na f 2-Propanol 48 graphic file with name c6sc03699f-u5.jpg 21
8 t-BuONa tert-Butanol 48 graphic file with name c6sc03699f-u6.jpg 4
9 HONa H2O 24 graphic file with name c6sc03699f-u7.jpg 34 (1af), 26 (1ag)
10 MeONa H2O 24 graphic file with name c6sc03699f-u8.jpg 52 (1af), 21 (1ag)

aGeneral conditions: [2-(2-halophenyl)pyridine] = 20 mM, [alkoxide] = 40 mM, 0.5 mL solvent, 110 °C.

bCalculated with 1H-NMR spectroscopy using 1,3,5-trimethoxybenzene as the internal standard.

dIn parentheses, the yield of the ethoxide insertion product.

eIn parentheses, the yield after 48 h.

fThe alkoxide was generated in situ adding 2 equivalents of sodium tert-butoxide as a base.