Visible-light photoredox-catalyzed selective carboxylation of C(sp2)-F bonds in polyfluoroarenes with CO2

doi:10.1016/S1872-2067(22)64140-8

Abstract

Abstract:

Visible light-driven carboxylation with CO₂ have emerged as a sustainable and powerful way to transfer waste to treasure. However, it is still challenging for aryl fluorides due to the low reactivities of both C(sp²)-F bonds and CO₂. Herein, we report the first photocatalytic carboxylation of aryl C-F bonds with CO₂. The visible-light photoredox catalysis enables selective carboxylation of strong C(sp²)-F bonds in diverse polyfluoroarenes, such as penta-, tetra-, and tri-fluoroarenes under mild conditions, providing a facile access to a series of important polyfluoroaryl carboxylic acids with good yields. In contrast to previous reports of direct capture of polyfluoroaryl radicals, mechanistic studies suggest that the reduction of fleeting polyfluoroaryl radicals into polyfluoroaryl anions might be involved in this transformation, which may open a new avenue for photocatalytic functionalization of aryl C-F bonds.

Key words: Carbon dioxide, Visible-light photoredox catalysis, Carboxylation, C-F functionalization, Polyfluoroarenes

Zhi-Yu Bo, Si-Shun Yan, Tian-Yu Gao, Lei Song, Chuan-Kun Ran, Yi He, Wei Zhang, Guang-Mei Cao, Da-Gang Yu. Visible-light photoredox-catalyzed selective carboxylation of C(sp²)-F bonds in polyfluoroarenes with CO₂[J]. Chinese Journal of Catalysis, 2022, 43(9): 2388-2394.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(22)64140-8

https://www.cjcatal.com/EN/Y2022/V43/I9/2388

Figures/Tables 8

Scheme 1. Visible-light photocatalytic carboxylation of aryl (pseudo)halides.

Fig. 1. Selected examples of polyfluoroaryl acids and derivatives.

Table 1 Optimization of reaction conditions.

Entry	Variations form the standard	Yield (%)
1	none	78
2	w/o [Ir(ppy)₂(dtbbpy)]PF₆	trace
3	w/o light	N.D.
4	N₂ instead of CO₂	trace
5	w/o HCO₂K	< 5
6	quinuclidine as HAT reagent	< 5
7	w/o DABCO	37
8	w/o base	44
9	DMSO instead of DMF	(43)
10	Cs₂CO₃ (2.5 eq.) instead of CsF/Cs₂CO₃	61
11	CsF (2.5 eq.) instead of CsF/Cs₂CO₃	62

Scheme 2. Substrate scopes of pentafluoroarenes. Reaction conditions as shown in Table 1, entry 1. Regioselectivity was detected by crude GC. “Others” refers to ortho and meta regioisomers. a 42 h. b HCO2K (2.5 eq.) was used. c CsF (2.5 eq.), Cs2CO3 (1.5 eq.) were used. 30 h. d 48 h. e Cs2CO3 (2.5 eq.) was used as sole base. DMF (2 mL) and DMSO (300 μL) were used as co-solvent. 34 h.

Scheme 3. Substrate scope of trifluoroarenes. Reaction conditions: 3 (0.2 mmol, 1 eq.), [Ir(ppy)2](dtbbpy)]PF6 (2.5 mol%), DABCO (60 mol%), HCO2K (2.5 eq.), Cs2CO3 (2.5 eq.), DMF (2 mL), DMSO (300 μL), irradiated by 30 W blue LEDs at room temperature under CO2 (1 atm) for 38 h. Isolated yields. Single regioisomer was detected. a 32 h. b HCO2K (3 eq.) was used. c DMSO (2 mL) was used as sole solvent. 24 h. d [Ir(ppy)2](dtbbpy)]PF6 (2 mol%), DABCO (50 mol%) and HCO2K (2 eq.) were used. 32 h. e HCO2K (3.5 eq.) was used.

Scheme 4. Substrate scope of tetrafluoroarenes. Reaction conditions as shown in Table 1, entry 1. Regioselectivity was detected by crude GC. a HCO2K (3 eq.) was used.

Scheme 5. Control experiments.

Scheme 6. Proposed mechanism.

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Visible-light photoredox-catalyzed selective carboxylation of C(sp²)-F bonds in polyfluoroarenes with CO₂

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