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. 2020 Jun 15;16:1305–1312. doi: 10.3762/bjoc.16.111

Table 2.

Influence of bases on the photoredox trifluoromethoxylation in batch and flow.

graphic file with name Beilstein_J_Org_Chem-16-1305-i002.jpg

Entry Equiv of substrate Сonc. of 1 (M) Base Yield (%)a

organic/soluble bases

1 10 0.08 (Bu4N)H2PO4, 1 equiv 20
2 10 0.08 (Bu4N)H2PO4, 1 equiv 6 (flow)
3 25 0.04 DIPEA, 1 equiv 18
4 25 0.04 DBU, 1 equiv 14 (flow)
5 25 0.04 (Bu4N)OAc, 1 equiv 0 (flow)

inorganic bases

6 25 0.04 K2CO3, 1 equiv 54
7 25 0.04 K2HPO4, 1 equiv 86
8 25 0.04 K2HPO4, 1 equiv 7b (flow)
9 10 0.04 K2HPO4, 1 equiv 68
10 10 0.08 K2HPO4, 1 equiv 78
11 10 0.08 K2HPO4, 0.5 equiv 78
12 10 0.08 K2HPO4, 0.25 equiv 77
13 10 0.08 K2HPO4, 2 equiv 70
14 10 0.08 KH2PO4, 1 equiv 89
15 10 0.08 KH2PO4, 1 equiv 75c (flow)
16 10 0.08 KH2PO4, 0.5 equiv 64
17 10 0.08 KH2PO4, 0.25 equiv 63
18 10 0.08 KH2PO4, 2 equiv 78
19 10 0.08 K3PO4, 1 equiv 54

a 19F NMR yields are reported; b 100 equiv of H2O added; c 5 minutes of irradiation in batch before flow reaction.