Reaction optimizationa.
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Entry | Solvent | Amine/HF | Catalyst loading [mol%] | Yieldb [%] |
1 | CHCl3 | 1 : 4.5 | 20 | 72 |
2 | CHCl 3 | 1 : 6.0 | 20 | >95 |
3 | CHCl3 | 1 : 7.5 | 20 | 94 |
4 | CHCl3 | 1 : 9.23 | 20 | 87 |
5 | CHCl3 | 1 : 6.0 | 10 | 87 |
6 | CHCl3 | 1 : 6.0 | 5 | 79 |
7 | DCM | 1 : 6.0 | 20 | >95 |
8 | DCE | 1 : 6.0 | 20 | 93 |
9 | ETFA | 1 : 6.0 | 20 | 84 |
10 | MeCN | 1 : 6.0 | 20 | 50 |
11 | CHCl3 | 1 : 6.0 | 0 | <5 |
Standard reaction conditions: 1a (0.2 mmol), Selectfluor® (1.5 equiv.), amine : HF source (0.5 mL), solvent (0.5 mL), p-TolI, 24 h, rt.
Determined by 19F NMR using α,α,α-trifluorotoluene as internal standard.