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A photocatalytic method for the regioselective carboxylation of azine C–H bonds using CO2

The visible-light-driven thiolate-catalysed carboxylation of C(sp2)–H bonds in azines using CO2 is demonstrated. This procedure can be applied to various azine substrates to obtain a range of N-heteroaromatic carboxylic acids with different functionalities, including bioactive molecules and carboxylated N-ligands.

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Fig. 1: Examples of N-heteroaromatic carboxylic acids and a possible mechanism for the visible-light-driven thiolate-catalysed carboxylation of C−H bonds in azines with CO2.

References

  1. Liu, Q., Wu, L., Jackstell, R. & Beller, M. Using carbon dioxide as a building block in organic synthesis. Nat. Commun. 6, 5933 (2015). A review article that presents the application of CO2 in organic synthesis.

    Article  ADS  PubMed  Google Scholar 

  2. Crisenza, G. E. M., Mazzarella, D. & Melchiorre, P. Synthetic methods driven by the photoactivity of electron donor–acceptor complexes. J. Am. Chem. Soc. 142, 5461–5476 (2020). A review article that presents the application of EDA complexes in organic synthesis.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Wang, S., Wang, H. & König, B. Light-induced single-electron transfer processes involving sulfur anions as catalysts. J. Am. Chem. Soc. 143, 15530–15537 (2021). A review article that presents sulfur anions as catalysts in photoredox catalysis.

    Article  CAS  PubMed  Google Scholar 

  4. Ye, J.-H., Ju, T., Huang, H., Liao, L.-L. & Yu, D.-G. Radical carboxylative cyclizations and carboxylations with CO2. Acc. Chem. Res. 54, 2518–2531 (2021). A review article that presents visible-light-driven carboxylation using CO2.

    Article  CAS  PubMed  Google Scholar 

  5. Huang, H. et al. Visible-light-driven anti-Markovnikov hydrocarboxylation of acrylates and styrenes with CO2. CCS Chem. 2, 1746–1756 (2020). This paper reports the visible-light-driven thiolate-catalysed hydrocarboxylation of alkenes with CO2 via EDA complex formation.

    Google Scholar 

  6. Miao, M. et al. Visible-light-driven thio-carboxylation of alkynes with CO2: facile synthesis of thiochromones. Sci. China Chem. 66, 1457–1466 (2023). This paper reports the visible-light-driven thio-carboxylation of alkynes with CO2 via EDA complex formation.

    Article  CAS  Google Scholar 

Download references

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This is a summary of: Jiang, Y.-X. et al. Visible-light-driven synthesis of N-heteroaromatic carboxylic acids by thiolate-catalysed carboxylation of C(sp²)–H bonds using CO2. Nat. Synth. https://doi.org/10.1038/s44160-023-00465-6 (2024).

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A photocatalytic method for the regioselective carboxylation of azine C–H bonds using CO2. Nat. Synth 3, 305–306 (2024). https://doi.org/10.1038/s44160-023-00466-5

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