Catalysis Based on C−I⋅⋅⋅π Halogen Bonds: Electrophilic Activation of 2-Alkenylindoles by Cationic Halogen-Bond Donors for [4+2] Cycloadditions

Satoru Kuwano, Takumi Suzuki, Masahiro Yamanaka, Ryosuke Tsutsumi, Takayoshi Arai

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

Homo- and cross-[4+2] cycloadditions of 2-alkenylindoles, catalyzed by cationic halogen-bond donors, were developed. Under mild reaction conditions, 3-indolyl-substituted tetrahydrocarbazole derivatives were obtained in good to excellent yields. Experimental and quantum calculation studies revealed that the electrophilic activation of 2-alkenylindoles was achieved by C−I⋅⋅⋅π halogen bonds.

Original languageEnglish
Pages (from-to)10220-10224
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number30
DOIs
Publication statusPublished - 2019 Jul 22
Externally publishedYes

Keywords

  • cycloaddition
  • density-functional calculations
  • halogen bonding
  • heterocycles
  • noncovalent bonds

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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