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. 2011 Oct 17;7:1421–1435. doi: 10.3762/bjoc.7.166

Table 2.

Effect of catalyst loading, temperature, and water content on the fluorination of 1 with catalyst K1.a

graphic file with name Beilstein_J_Org_Chem-07-1421-i002.jpg

Entry K1 (mol %) T (°C) Additives (mol %) t (h) ee (%)

1 1.2 rt 45b 25.2
2 5 rt 6 26.6
3 10 rt 2 26.5
4 20 rt <2 25.5
5 50 rt <0.3 23.4
6 100 rt <0.3 22.4
7 5 rt MS 3 Å 6 27
8 5 rt 6 28.5c
9 5 rt H2O (5) 10 28.5
10 5 rt H2O (50) >12d 28
11 5 rt H2O (1000) e
12 5 0 16 32
13 5 rt <8 28
14 5 40 <2 23
15 5 60 0.1f 18

aAll reactions were performed in reagent grade acetonitrile stored over 3 Å molecular sieves and run to complete conversion (TLC), unless otherwise mentioned. bReaction stopped before complete conversion. cEntries 1–6 vs 7–11 vs 12–15 were run with different batches of F–TEDA, solvent and catalyst, leading to small selectivity deviations under seemingly identical conditions. d50% conversion. eNo reaction. fConversion stopped at 80%.