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. 2021 Feb 3;11(11):6099–6106. doi: 10.1039/d0ra09827b

Experimental evidencea,b.

graphic file with name d0ra09827b-u5.jpg
Entry F Solvent Time Yieldc (%)
2 11 10a 12a 13
1 TBAF CD3OD 17 h 10 22 10 41 17
2 TBAF CD3CN/CD3OD (6.5 : 1) 20 min 36 23 21 15 5
3 CsF CD3CN/CD3OD (6.5 : 1) 5 h 7.8 51.5 4.2 34.9 1.6
4 CsF CD3CN/CD3OD (17.8 : 1) 5 h 34 38 12 15 1
5 CsF CD3CN/(CD3)3COD (6.5 : 1) 5 h 31.5 65.9 0
6 CsF CD3CN/(CD3)3COD (17.8 : 1) 5 h 65 35 0
a

All reactions were carried out on a 0.084 mmol reaction scale of triazolium precursor 1 in 0.75 mL of solvent in a sealed NMR tube. TBAF·3H2O or CsF (6 equiv.) was used as F source.

b

Traces of 10b and 12b were detected by 19F NMR.

c

19F NMR yield.