. Author manuscript; available in PMC: 2021 Mar 30.

Published in final edited form as: Nat Catal. 2020 Aug 24;3(9):734–742. doi: 10.1038/s41929-020-0495-0

Table 1.

Reaction optimization for arene deoxyfluorination


entry	deviation from standard conditions	yield (%)^a
1	none	79^b
2	KF (5.0 equiv)	78^b
3	TBAHSO₄ (0.5 equiv)	73^c
4	TBAHSO₄ (0.25 equiv)	53^c
5	TBAHSO₄ (0.5 equiv), DCM:H₂O (10:1), KF (5.0 equiv)	48^c
6	TBAHSO₄ (0.5 equiv), DCM:H₂O (10:1), KF (10.0 equiv)	67^c
7	TBAHSO₄ (0.5 equiv), DCM:H₂O (10:1), CsF (3.0 equiv)	52^c
8	No photocatalyst	N.D.^c
9	No irradiation	9
10	TBAHSO₄ (0.5 equiv), DCM:H₂O (2.7:1), CsF (10.0 equiv)	35^c
11	TBAHSO₄ (0.5 equiv), DCM:H₂O (1:1), CsF (10.0 equiv)	23^c
12	TBAHSO₄ (0.5 equiv), DCM:t-BuOH (10:1), CsF (10.0 equiv)	5^c
13	TBAHSO₄ (0.5 equiv), DCM:t-BuOH:H₂O (19:1:2), CsF (10.0 equiv)	67^c
14	TBAHSO₄ (0.5 equiv), DCM:t-BuOH:H₂O (100:1:9), CsF (10.0 equiv)	71^c
15	w/o TBAHSO₄, DCM:t-BuOH:H₂O (100:1:9), CsF (10.0 equiv)	22^c
16	w/o TBAHSO₄, DCM:H₂O (10:1) TBAF•H₂O (10.0 equiv)	9^c
17	KHF₂ (10.0 equiv) instead of CsF	27^c

GC yields using 1,2 dichlorobenzene as an internal standard;

427 nm LEDs;

455 nm LEDs. See Supplementary Table 1 for full optimization details.