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Palladium-catalyzed cascade of aza-Wacker and Povarov reactions of aryl amines and 1,6-dienes for hexahydro-cyclopenta[b]quinoline framework

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  • Jiahao Wu

    (South China University of Technology)

  • Xiangwen Tan

    (South China University of Technology)

  • Wanqing Wu

    (South China University of Technology)

  • Huanfeng Jiang

    (South China University of Technology)

Abstract

Palladium catalyzed tandem reaction represents a one-pot synthetic approach to efficiently synthesize complex functionalized molecules while reducing synthetic steps, aligning with the principles of green chemistry. However, achieving a direct cascade of the aza-Wacker and Povarov reactions in one-pot synthesis presents a challenge due to substrate compatibility issues between the two reactions. In this work, we describe an aza-Wacker/Povarov reaction employing a highly electrophilic palladium catalyst, which effectively converts anilines and 1,6-dienes into hexahydro-cyclopenta[b]quinolines. The optimized conditions yield up to 79%, with a diastereoselectivity > 20:1. Substrate range testing reveals compatibility with various sensitive functional groups, and successful late-stage modifications are performed on several natural products and drug molecules, demonstrating the versatility and practicality of the method. Additionally, a preliminary investigation into the reaction mechanism suggests an aza-Wacker process followed by a Povarov process.

Suggested Citation

  • Jiahao Wu & Xiangwen Tan & Wanqing Wu & Huanfeng Jiang, 2024. "Palladium-catalyzed cascade of aza-Wacker and Povarov reactions of aryl amines and 1,6-dienes for hexahydro-cyclopenta[b]quinoline framework," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-51173-4
    DOI: 10.1038/s41467-024-51173-4
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    References listed on IDEAS

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    1. Chengwen Li & Ying-Bo Shao & Xi Gao & Zhiyuan Ren & Chenhao Guo & Meng Li & Xin Li, 2023. "Enantioselective synthesis of chiral quinohelicenes through sequential organocatalyzed Povarov reaction and oxidative aromatization," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
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