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Chiral acid-catalysed enantioselective C−H functionalization of toluene and its derivatives driven by visible light

Author

Listed:
  • Fuyuan Li

    (Henan University)

  • Dong Tian

    (Henan University)

  • Yifan Fan

    (Henan University
    Henan Normal University)

  • Richmond Lee

    (Singapore University of Technology and Design)

  • Gang Lu

    (Shandong University)

  • Yanli Yin

    (Henan University)

  • Baokun Qiao

    (Henan University)

  • Xiaowei Zhao

    (Henan University)

  • Ziwei Xiao

    (Henan University)

  • Zhiyong Jiang

    (Henan University
    Henan Normal University)

Abstract

Toluene and its derivatives are petroleum-derived raw materials produced from gasoline by catalytic reformation. These abundant chemical feedstocks are commonly used as solvents in organic synthesis. The C(sp3)−H functionalization of these unactivated substrates has been widely used to directly introduce benzylic motifs into diverse molecules to furnish important compounds. Despite these advances, progress in asymmetric catalysis remains underdeveloped. Here, we report photoinduced radical-based enantioselective C(sp3)−C(sp3) coupling reactions of activated ketones with toluene and its derivatives by means of chiral acid catalysis. With a La(OTf)3/pybox complex catalyst, a variety of chiral 3-hydroxy-3-benzyl-substituted 2-oxindoles, including many conventionally difficult-to-access variants, are obtained directly from isatins in high yields with good to excellent enantioselectivities. Acenaphthoquinone is also compatible with the use of a chiral phosphoric acid (CPA) catalyst, leading to another series of important enantioenriched tertiary alcohols.

Suggested Citation

  • Fuyuan Li & Dong Tian & Yifan Fan & Richmond Lee & Gang Lu & Yanli Yin & Baokun Qiao & Xiaowei Zhao & Ziwei Xiao & Zhiyong Jiang, 2019. "Chiral acid-catalysed enantioselective C−H functionalization of toluene and its derivatives driven by visible light," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-09857-9
    DOI: 10.1038/s41467-019-09857-9
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