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Highly regioselective synthesis of branched saturated aldehydes by tandem hydroformylation/isomerization/hydrogenation of 1-arylbutadienes

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Abstract

Rh-catalyzed tandem hydroformylation/isomerization/hydrogenation of various 1-arylbutadienes toward the corresponding branched saturated aldehydes were performed in the presence of monodentate phosphine ligand PPh3. After investigating different reaction parameters such as P-ligands and solvents, the conversion of substrates (including electron withdrawing and electron donating groups on aromatic rings, up to 99%) and chemical/regioselectivity of the target products (up to 98% and 99/1 for B/L) were improved using DMF as solvent. The [Rh(cod)Cl]2/PPh3 catalytic system had good substrate universality in terms of substituents on the phenyl ring and provided a simple synthesis method for branched saturated aldehydes.

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Data availability

The data that support the findings of this study are available in Supporting Information, which associated with the experiments can be found in the online version.

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (No. 21901250).

Author information

Author notes

  1. Huibing Shi and Peng Wang have contributed equally to this work.

Authors and Affiliations

  1. Shandong Chambroad Petrochemicals Co., Ltd, Binzhou, 256500, Shandong, China

    Huibing Shi, Peng Wang, Yaozong Yan & Guiai Yang

  2. School of Life Sciences, Henan University, Kaifeng, 475004, Henan, China

    Haigang Wu

  3. School of Biomedical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China

    Haigang Wu

Authors
  1. Huibing Shi
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  2. Peng Wang
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  3. Yaozong Yan
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  4. Guiai Yang
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  5. Haigang Wu
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Correspondence to Peng Wang or Haigang Wu.

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Shi, H., Wang, P., Yan, Y. et al. Highly regioselective synthesis of branched saturated aldehydes by tandem hydroformylation/isomerization/hydrogenation of 1-arylbutadienes. Monatsh Chem 155, 731–738 (2024). https://doi.org/10.1007/s00706-024-03224-1

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