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. Author manuscript; available in PMC: 2015 Oct 11.
Published in final edited form as: Chem Commun (Camb). 2014 Oct 11;50(79):11701–11704. doi: 10.1039/c4cc05650g

Table 1.

Effects of the light source and the ketone catalyst on the benzylic fluorination of 1 and 2

graphic file with name nihms622911t1.jpg

Entry Substrate Catalyst Light source Time Yield[i]
1 1 9-fluorenone 1 × CFL[a] 24 h 89% (85%)[j]
2 1 1 × CFL[a] 24 h 0%
3 2 9-fluorenone 1 × CFL[a] 24 h 80% (76%)[j]
4 2 1 × CFL[a] 30 h 89%
5 2 16 × RPR-3000Å[b] 30 min 46%
6 2 16 × RPR-3500Å[c] 1 h 73%
7 2 16 × RPR-4190Å[d] 6 h 96%
8 1 acetophenone 16 × RPR-4190Å[d] 6 h 88%
9 1 acetophenone 16 × RPR-4190Å[d,e] 20 h 70%
10 1 acetophenone 16 × RPR-4190Å[d,f] 20 h 0%
11 1 acetophenone 1 × violet LED[g] 3 h 85%
12 1 acetophenone 1 × CFL[a] 20 h 61%
13 1 acetophenone 1 × CFL[a,e] 20 h 50%
14 1 acetophenone 1 × CFL[a,f] 20 h 0%
15 1 acetone 1 × CFL[a} 20 h 0%
16 1 acetophenone [h] 24 h 0%
[a]

19 W, household lamp.

[b]

21 W, 250–375 nm.

[c]

24 W, 300–420 nm.

[d]

375–465 nm.

[e]

With a 375 nm longpass filter.

[f]

With a 400 nm logpass fileter.

[g]

9 W, 370–405 nm.

[h]

50 °C.

[i]

Determined by 19F NMR using C6H5F as an external standard.

[j]

Isolated yield.