Photocatalytic carboxylation of styrenes with CO2 via C=C double bond cleavage

doi:10.1016/S1872-2067(23)64583-8

Abstract

Abstract:

Catalytic cleavage of C=C double bonds in alkenes is highly important to convert feedstocks into high-value compounds. However, these approaches are mainly limited to oxidative cleavage of alkenes with excess oxidants and redox-neutral alkene metathesis. In contrast, reductive C=C double bond cleavage and functionalization have not been reported. Herein, we report a novel visible-light photoredox-catalyzed carboxylation of styrenes with CO₂ via reductive C=C double bond cleavage. The use of dicyclohexylmethylamine as scission reagent is the key to the success. Different from previous homologation reactions with CO₂, this protocol enabled exchange of the carbon of styrenes with CO₂, affording important aryl acetic acids via C=C double bond cleavage. Moreover, preliminary mechanistic investigation and DFT calculations shed light on the reaction mechanism, disclosing aminomethyl-carboxylation intermediate, benzylic radicals and carbanions as key intermediates in the reaction.

Key words: Carbon dioxide, Visible-light photoredox catalysis, C=C bond cleavage, Carboxylation, Aryl acetic acids

Ke-Gong Cao, Tian-Yu Gao, Li-Li Liao, Chuan-Kun Ran, Yuan-Xu Jiang, Wei Zhang, Qi Zhou, Jian-Heng Ye, Yu Lan, Da-Gang Yu. Photocatalytic carboxylation of styrenes with CO₂ via C=C double bond cleavage[J]. Chinese Journal of Catalysis, 2024, 56: 74-80.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(23)64583-8

https://www.cjcatal.com/EN/Y2024/V56/I1/74

Figures/Tables 7

Fig. 1. Visible-light photoredox-catalyzed carboxylation with CO2 via reductive cleavage of C=C bond in styrenes.

Table 1 Optimization of reaction conditions.a


Entry	Variations	2a ^b (%)
1	none	91 (88)
2	DIPEA instead of Cy₂NMe	47
3	Et₃N instead of Cy₂NMe	17
4 5	4CzIPN instead of 3DPA2FBN 4DPAIPN instead of 3DPA2FBN	8 74
6	fac-Ir(ppy)₃ instead of 3DPA2FBN	2
7	KOMe instead of HCOOK	74
8	K₂CO₃ instead of HCOOK	71
9	DMSO instead of DMAc	72
10	NMP instead of DMAc	70
11	w/o CO₂	N. D.
12	w/o 3DPA2FBN	N. D.
13	w/o Cy₂NMe	N. D.
14	w/o Light	N. D.
15	w/o HCOOK	78

Table 2 Substrate scope of 1,1-diarylalkenes a.

Table 3 Substrate scope of mono-aryl-substituted alkenes a.

Scheme 1. Mechanistic studies.

Scheme 2. Calculated free energy profiles. Profiles of transformation of carbon-carboxylated intermediate. The values given in kcal/mol are the relative free energies calculated by the M06/6-311+G(d,p)//B3LYP/6-31+G(d) method in DMAc solvent.

Scheme 3. Possible mechanism.

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Photocatalytic carboxylation of styrenes with CO₂ via C=C double bond cleavage

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