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Catalytic asymmetric [4 + 2] dearomative photocycloadditions of anthracene and its derivatives with alkenylazaarenes

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Listed:
  • Dong Tian

    (Henan University, Jinming Campus)

  • Wenshuo Shi

    (Henan University, Jinming Campus)

  • Xin Sun

    (Henan University, Jinming Campus)

  • Xiaowei Zhao

    (Henan University, Jinming Campus)

  • Yanli Yin

    (Henan Normal University
    Henan University of Technology)

  • Zhiyong Jiang

    (Henan University, Jinming Campus
    Henan Normal University)

Abstract

Photocatalysis through energy transfer has been investigated for the facilitation of [4 + 2] cycloaddition reactions. However, the high reactivity of radical species poses a challenging obstacle to achieving enantiocontrol with chiral catalysts, as no enantioselective examples have been reported thus far. Here, we present the development of catalytic asymmetric [4 + 2] dearomative photocycloaddition involving anthracene and its derivatives with alkenylazaarenes. This accomplishment is achieved by utilizing a cooperative photosensitizer and chiral Brønsted acid catalysis platform. Importantly, this process enables the activation of anthracene substrates through energy transfer from triplet DPZ, thereby initiating a precise and stereoselective sequential transformation. The significance of our work is highlighted by the synthesis of a diverse range of pharmaceutical valuable cycloadducts incorporating attractive azaarenes, all obtained with high yields, ees, and drs. The broad substrate scope is further underscored by successful construction of all-carbon quaternary stereocenters and diverse adjacent stereocenters.

Suggested Citation

  • Dong Tian & Wenshuo Shi & Xin Sun & Xiaowei Zhao & Yanli Yin & Zhiyong Jiang, 2024. "Catalytic asymmetric [4 + 2] dearomative photocycloadditions of anthracene and its derivatives with alkenylazaarenes," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-48982-y
    DOI: 10.1038/s41467-024-48982-y
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    1. Evan M. Sherbrook & Matthew J. Genzink & Bohyun Park & Ilia A. Guzei & Mu-Hyun Baik & Tehshik P. Yoon, 2021. "Chiral Brønsted acid-controlled intermolecular asymmetric [2 + 2] photocycloadditions," Nature Communications, Nature, vol. 12(1), pages 1-7, December.
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