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Chinese Journal of Organic Chemistry >

0 260518

DOI: https://doi.org/10.6023/cjoc202601024

ARTICLE

Light-induced intramolecular cyclization through insertion of N-tosylhydrazone into C(sp3)-H and C=C bonds

  • Li Jin-Rui ,
  • Wei Ke-Yue ,
  • Wang Hua
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  • aDepartment of Chemistry, School of Pharmacy, The Fourth Military Medical University (Air Force Medical University), Xi'an Shaaxi 710032;
    bMilitary Medical Innovation Center, The Fourth Military Medical University (Air Force Medical University), Xi'an, Shaaxi 710032
*E-mail: wanghua87@fmmu.edu.cn

Received date: 2026-01-19

  Revised date: 2026-03-18

  Online published: 2026-05-14

Supported by

National Natural Science Foundation of China (No. 22201303), Sanqin Talents Introduction Program of Shaanxi Province - Youth Project.

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Abstract

We report herein a light-promoted, transition-metal-free intramolecular C(sp³)-H/C=C insertion cyclization of N-tosylhydrazones has been developed. Using cesium carbonate as the base, the reaction proceeds under mild conditions via photoexcited hydrazone anions to generate highly reactive alkyl diazo intermediates. This enables highly selective insertion into both intramolecular C(sp³)-H bonds and C=C double bonds, efficiently constructing over 20 differently substituted [4.1.0]-fused bicyclic and benzofuran frameworks with yields up to 85%. The strategy exhibits broad functional group tolerance and scalability to gram-scale. Mechanistic studies indicate that the formation of photoexcited hydrazone anions is the key step in the reaction pathway.

Key words： N-tosylhydrazone; photoexcited anions; carbene insertion into C(sp³)-H bonds; carbene insertion into C=C bonds; intramolecular cyclization

Cite this article

Li Jin-Rui , Wei Ke-Yue , Wang Hua . Light-induced intramolecular cyclization through insertion of N-tosylhydrazone into C(sp3)-H and C=C bonds[J]. Chinese Journal of Organic Chemistry, 0 : 260518 . DOI: 10.6023/cjoc202601024

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