Visible-light photoredox-catalyzed carboxylation of benzyl halides with CO2: Mild and transition-metal-free

doi:10.1016/S1872-2067(21)63859-7

Abstract

Abstract:

The visible-light photoredox-catalyzed carboxylation of benzyl chlorides and bromides with CO₂ has been reported. With inexpensive organic dyes as photocatalysts and amines as electron donors, this carboxylation proceeds well in the absence of sensitive organometallic reagents, transition metal catalysts, or metallic reductants. A wide range of commercially available and inexpensive benzyl halides undergo such carboxylation to give valuable aryl acetic acids, including several pharmaceutical molecules and drug precursors, in moderate to high yields. Moreover, this reaction features mild reaction conditions (one atmospheric pressure of CO₂ and room temperature), broad substrate scope, good functional group tolerance, easy scalability, and low catalyst loading, thus providing an efficient approach for the assembly of aryl acetic acids.

Key words: Carbon dioxide, Visible-light photoredox catalysis, Carboxylation, Aryl acetic acids, Benzyl halides

Ke Jing, Ming-Kai Wei, Si-Shun Yan, Li-Li Liao, Ya-Nan Niu, Shu-Ping Luo, Bo Yu, Da-Gang Yu. Visible-light photoredox-catalyzed carboxylation of benzyl halides with CO₂: Mild and transition-metal-free[J]. Chinese Journal of Catalysis, 2022, 43(7): 1667-1673.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(21)63859-7

https://www.cjcatal.com/EN/Y2022/V43/I7/1667

Figures/Tables 10

Fig. 1. Representative aryl acetic acids.

Scheme 1. Reductive carboxylation of benzyl halides with CO2.

Table 1 Optimization of reaction conditions.

Scheme 2. Substrate scope of benzyl chlorides. Reaction conditions as presented in Table 1, entry 1. a 16 h. b 3 mol% 4CzIPN, 2.0 equiv. TMEDA, 2.0 equiv. Cs2CO3. c 2 mol% 4CzIPN. d The ratio of 2h to phenylacetic acid is 14.3:1. e 3 mol% 4DPAIPN, 24 h. f The ratio of 2q to phenylacetic acid is 16.7:1. g 5 h. h 6 h, then MeI (3 equiv.), 65 °C, 3 h. i 5 mL N,N-dimethylacetamide (DMAc) used instead of DMF. j 3 equiv. TMEDA. k 10 h. l 2 h. m 0.5 mol% 4DPAIPN.

Scheme 3. Substrate scope of benzyl bromides. Reaction conditions: 3 (0.2 mmol), 1 atm CO2, 4DPAIPN (0.002 mmol), TMEDA (0.12 mmol), Cs2CO3 (0.4 mmol), DMF (2 mL), 30 W blue LED, rt, 8 h. a 16 h. b Reaction conditions as shown in Table 1, entry 1.

Scheme 4. Reaction of allyl chloride 5. Reaction conditions as presented in Table 1, entry 1. The yield and ratio were determined by crude 1H NMR.

Scheme 5. Control experiments to confirm benzylic radical and benzylic anion intermediates.

Fig. 2. Reaction profiles of compounds 1a and 11. Reaction conditions for 1a as presented in Table 1, entry 1. Reaction conditions for 11: 11 (0.2 mmol), other conditions as presented in Table 1, entry 1 except the addition of TMEDA.

Fig. 3. Stern-Volmer luminescence studies.

Scheme 6. Plausible mechanisms.

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Visible-light photoredox-catalyzed carboxylation of benzyl halides with CO₂: Mild and transition-metal-free

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