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Synthesis
DOI: 10.1055/a-2733-4012
Paper

Photocatalytic Regioselective Hydroboration of Indoles and Benzofurans with N-Heterocyclic Carbene Boranes

Authors

  • Yubing Pang

    1   School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, China (Ringgold ID: RIN12474)

  • Zongyang Ma

    1   School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, China (Ringgold ID: RIN12474)
    2   College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, China (Ringgold ID: RIN12576)

  • Juntao Ye

    1   School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, China (Ringgold ID: RIN12474)

Supported by: National Natural Science Foundation of China 22371180
Further Information
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Dearomative hydroboration of arenes using nucleophilic boryl radicals provides a powerful strategy for converting flat, abundant arenes into valuable three-dimensional organoboron architectures. While such reactions are well-established for electrondeficient arenes, analogous transformation of electron-rich heteroarenes remains challenging due to polarity mismatch. Herein, we report a photocatalytic approach that enables regioselective, dearomative hydroboration of both electron-rich and electrondeficient indoles and benzofurans using N-heterocyclic carbene (NHC) boranes. Density functional theory calculations indicate that C2-addition of the boryl radical is kinetically favored over C3-addition, and that the addition step becomes irreversible due to a subsequent low-barrier hydrogen atom transfer event.



Publication History

Received: 22 September 2025

Accepted after revision: 27 October 2025

Accepted Manuscript online:
27 October 2025

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