Chlorine radical-mediated photocatalytic C(sp3)-H bond oxidation of aryl ethers to esters

doi:10.1016/S1872-2067(23)64615-7

Abstract

Abstract:

The C(sp³)-H functionalization of naturally abundant alkanes is of great importance, whereas C-H bond oxidation of aryl ethers in a redox-neutral and environmental-friendly manner remains a challenge. Herein, we report a novel method of visible-light-driven C(sp³)-H bond oxidation of aryl ethers selectively into ester products using oxygen as the oxidant. During the photocatalytic reaction using Mes-10-phenyl-Acr⁺-BF₄^- catalyst, chlorine radicals are generated from a wide variety of chloride sources and can effectively activate aryl ether C(sp³)-H bonds into alkyl radicals through the hydrogen atom transfer process. Aryl ethers with different substituents can be oxidized to esters in good to excellent yields. This work presents a new photocatalytic strategy for C(sp³)-H oxidation of aryl ethers in a convenient and green manner.

Key words: Chlorine radical, Photocatalysis, C(sp³)-H bond, Catalytic oxidation, Aryl ethers

Yuting Liu, Beili Nie, Ning Li, Huifang Liu, Feng Wang. Chlorine radical-mediated photocatalytic C(sp³)-H bond oxidation of aryl ethers to esters[J]. Chinese Journal of Catalysis, 2024, 58: 123-128.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(23)64615-7

https://www.cjcatal.com/EN/Y2024/V58/I3/123

Figures/Tables 7

Scheme 1. Strategies for C(sp3)-H bond functionalization.

Fig. 1. Photocatalytic C(sp3)-H bond oxidation of anisole under different conditions. (a) Effects of different solvents. (b) H+ cation detection in the CH2Cl2, MeCN and CH2Cl2 + MeCN (v/v = 1: 1) mixed solvents after reaction for 0.5 h. (c) Optimizations using various chloride additives. Reaction conditions: anisole (0.1 mmol), PC-Mes (2.5 mol%), [Cl] (20 mol%), 455 nm LEDs, solvent (1.0 mL), 0.2 MPa of O2, 3 h. PC-Mes = Mes-10-phenyl-Acr+-BF4-.

Fig. 2. (A) Kinetic profile. (B) Control experiments. Standard conditions: anisole (0.1 mmol), PC-Mes (2.5 mol%) and LiCl (20 mol%) were irradiated using 455 nm LEDs in MeCN (1.0 mL) for 3 h under 0.2 MPa of O2.

Fig. 3. Mechanistic investigations. Standard conditions: substrate (0.1 mmol), PC-Mes (2.5 mol%) and LiCl (20 mol%) were irradiated using 455 nm LEDs in MeCN (1.0 mL) under 0.2 MPa of O2.

Scheme 2. Proposed mechanism for C(sp3)-H bond oxidation of aryl ethers by chlorine radical.

Scheme 3. Scope of photocatalytic C(sp3)-H bond oxidation of aryl ethers. a Reaction conditions: substrate 1a?1p, 1q (0.1 mmol), PC-Mes (2.5 mol%) and LiCl (20 mol%) were irradiated using 455 nm LEDs in MeCN (1.0 mL) for 5 h under 0.2 MPa of O2. b The yield of 2a in parentheses. c Run for 2 h. d Run for 12 h. e Run for 3 h. f Run for 0.3 h. The yield of chroman-2-one (2g’) were determined by 1H-NMR in parentheses. g Run for 8 h. h Run for 4 h. i Run for 10 h. j Run for 6 h.

Scheme 4. Gram-scale reaction for C(sp3)-H bond oxidation of anisole.

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Chlorine radical-mediated photocatalytic C(sp³)-H bond oxidation of aryl ethers to esters

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