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PreprintCC BYChemRxiv

ICl-Mediated Iodocyclization of Electron-Deficient 1,5-Enynes to Functionalized Iodonaphthalenes

  • Takuji Kawamoto
  • Akane Tani
  • Ibuki Watanabe
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Abstract

Iodine-induced cyclizations of 1,5-enynes are generally limited to electron-rich alkenes. We report an ICl-mediated iodocyclization of 1,5-enynes bearing strongly electron-withdrawing vinyl-bis(perfluoroalkanesulfonyl)amide groups. A range of aryl-substituted enynes cyclized under mild conditions to give iodonaphthalenes in good yields with tolerance of halogen and carbonyl substituents. The products retain both the iodine atom and the bis(perfluoroalkanesulfonyl)amide unit. Suzuki-Miyaura coupling at the iodine site proceeds without cleavage of the sulfonimide moiety, demonstrating the utility of the products as precursors to functionalized naphthalenes.

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Cite

BibTeXRIS
BibTeX
@misc{kawamoto2026iclmediated,
  title = {{ICl-Mediated Iodocyclization of Electron-Deficient 1,5-Enynes to Functionalized Iodonaphthalenes}},
  author = {Takuji Kawamoto and Akane Tani and Ibuki Watanabe},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010741/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010741/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - ICl-Mediated Iodocyclization of Electron-Deficient 1,5-Enynes to Functionalized Iodonaphthalenes
AU  - Takuji Kawamoto
AU  - Akane Tani
AU  - Ibuki Watanabe
PY  - 2026
DA  - 2026/10/20
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010741/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010741/v1
AB  - Iodine-induced cyclizations of 1,5-enynes are generally limited to electron-rich alkenes. We report an ICl-mediated iodocyclization of 1,5-enynes bearing strongly electron-withdrawing vinyl-bis(perfluoroalkanesulfonyl)amide groups. A range of aryl-substituted enynes cyclized under mild conditions to give iodonaphthalenes in good yields with tolerance of halogen and carbonyl substituents. The products retain both the iodine atom and the bis(perfluoroalkanesulfonyl)amide unit. Suzuki-Miyaura coupling at the iodine site proceeds without cleavage of the sulfonimide moiety, demonstrating the utility of the products as precursors to functionalized naphthalenes.
ER  -