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. Author manuscript; available in PMC: 2021 Aug 7.
Published in final edited form as: Org Lett. 2020 Jul 29;22(15):5749–5752. doi: 10.1021/acs.orglett.0c02239

Table 1.

Fluorination Reaction Optimizations

graphic file with name nihms-1616692-t0002.jpg
entry [Cu] (mol%) BPhen (mol%) MeB(OH)2 (equiv) Li2CO3 (equiv) Conv (%) C–N (%) C–F (CF2)a (%)
1b,c CuCl (10) see Scheme 1A for conditions nd 76 nd
2c CuCl (10) 5 - - 24 19 4
3c CuCl (10) 5 2 - 100 42 -
4c CuCl (10) 5 2 3 100 44 21 (4)
5 CuCl (10) 5 2 3 100 25 40 (6)
6 CuCl (2) 1 2 3 86 4 74 (4)
7 CuOAc (2) 2.4 2 3 100 - 81 (11)
a

0.3 mmol scale. 1H NMR yields; int. std. = CH2Br2.

b

Reported results with ethylbenzene (ref. 6).

c

1,2-dichloroethane (DCE) used as the solvent.