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Visible-light-driven synthesis of N-heteroaromatic carboxylic acids by thiolate-catalysed carboxylation of C(sp²)–H bonds using CO2

Nature Synthesis volume 3, pages 394–405 (2024)Cite this article

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Abstract

Catalytic carboxylation of C–H bonds using CO2 is a sustainable and economic strategy to produce valuable carboxylic acids. However, this process presents challenges due to the low reactivity of C–H bonds and difficulties in controlling regioselectivity. Although progress has been made in this field, catalytic carboxylation of C–H bonds in azines with CO2 is still a challenge. Here we report a visible-light-driven, thiolate-catalysed carboxylation of azine C(sp2)–H bonds using CO2. A variety of azines, including quinolines, pyridines, phenanthroline, naphthyridine and acridine, can undergo catalytic carboxylation to give N-heteroaromatic carboxylic acids in good yields and with excellent regiocontrol. This method operates under mild and transition-metal-free reaction conditions, is tolerant of a wide range of functional groups and is scalable. The utility of this method is demonstrated by application to the synthesis of bioactive molecules, such as cinchophen and brequinar derivatives, and to the modification of commonly used nitrogen ligands, including bipyridines, terpyridine and phenanthroline. Mechanistic investigations reveal the formation of an electron donor–acceptor complex between the thiolate catalyst and azine substrate.

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Fig. 1: The importance and approaches of N-heteroaromatic carboxylic acids.
Fig. 2: Synthetic applications.
Fig. 3: Mechanistic investigations.
Fig. 4: Computational studies.

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Data availability

The authors declare that the data supporting the findings of this study are available within the Article and its Supplementary Information files. Crystallographic data for the structures reported in this Article have been deposited at the Cambridge Crystallographic Data Centre, under deposition numbers CCDC 2223857 (2z), 2219986 (6e) and 2268054 (6f). Copies of the data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures/.

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Acknowledgements

Financial support was provided by the National Natural Science Foundation of China (22225106 (D.-G.Y.), 22101191 (W.Z.), 22201027 (L.-L.L.)), Fundamental Research Funds from Sichuan University (2020SCUNL102 (D.-G.Y.)), the China Scholarship Council (202206240054 (W.Z.)) and the Fundamental Research Funds for the Central Universities. We thank X. Qi from Wuhan University for valuable discussion and help. We also thank X. Wang from the Analysis and Testing Center of Sichuan University and J. Li, Q. Zhang and D. Deng from the College of Chemistry at Sichuan University for compound testing.

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  1. These authors contributed equally: Yuan-Xu Jiang, Li-Li Liao.

Authors and Affiliations

  1. Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, P. R. China

    Yuan-Xu Jiang, Tian-Yu Gao, Wen-Hao Xu, Wei Zhang, Lei Song, Guo-Quan Sun, Jian-Heng Ye & Da-Gang Yu

  2. School of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing, P. R. China

    Li-Li Liao & Yu Lan

  3. West China School of Public Health and West China Fourth Hospital, Sichuan University, Chengdu, P. R. China

    Wei Zhang

  4. College of Chemistry, Institute of Green Catalysis, Zhengzhou University, Zhengzhou, P. R. China

    Yu Lan

  5. State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, P. R. China

    Da-Gang Yu

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Contributions

D.-G.Y. and J.-H.Y. conceived and designed the study. Y.-X.J., L.-L.L., J.-H.Y., Y.L. and D.-G.Y. wrote the paper. Y.-X.J., L.-L.L., T.-Y.G., W.-H.X., W.Z., L.S. and G.-Q. S. performed the experiments and mechanistic studies. L.-L.L. did the DFT calculations under supervision from Y.L. All authors contributed to the analysis and interpretation of the data.

Corresponding authors

Correspondence to Jian-Heng Ye, Yu Lan or Da-Gang Yu.

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Competing interests

D.-G.Y., Y.-X.J., T.-Y.G., L.-L.L., W.Z., L.S. and J.-H.Y. have applied for a Chinese patent (202210655523.4) relating to this work. The other authors declare no competing interests.

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Nature Synthesis thanks Juan Alegre-Requena and the other, anonymous, reviewer(s) for their contribution to the peer review of this work. Primary Handling Editor: Thomas West, in collaboration with the Nature Synthesis team.

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Supplementary information

Supplementary Information

Supplementary methods, references, Figs. 1–12 and Tables 1–3.

Supplementary Data 1

Crystallographic data for compound 2z (CCDC reference 2223857).

Supplementary Data 2

Crystallographic data for compound 6e (CCDC reference 2219986).

Supplementary Data 3

Crystallographic data for compound 6f (CCDC reference 2268054).

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Jiang, YX., Liao, LL., Gao, TY. et al. Visible-light-driven synthesis of N-heteroaromatic carboxylic acids by thiolate-catalysed carboxylation of C(sp²)–H bonds using CO2. Nat. Synth 3, 394–405 (2024). https://doi.org/10.1038/s44160-023-00465-6

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