1,4-Dehydrogenation with a Two-Coordinate Cyclic (Alkyl)(amino)silylene

Taichi Koike, Tomoyuki Kosai, Takeaki Iwamoto

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Cyclic (alkyl)(amino)silylene (CAASi) 1 has been found to successfully dehydrogenate 1,4-dihydroaromatic compounds containing various substituents to afford the corresponding aromatic compounds. The observed high substrate generality proves 1 to be a potential 1,4-dehydrogenation reagent for organic compounds. For the reaction with 9,10-dimethyl-9,10-dihydroanthracene, silylene 1 activated not only benzylic C−H bonds but also aromatic C−H bonds to yield a silaacenaphthene derivative, which is an unprecedented reaction of silylenes. The results of the experimental and computational study of the reaction of CAASi 1 with 9,10-dihydroanthracene and 1,4-cyclohexadiene are consistent with the notion that 1,4-dehydrogenation with CAASi 1 proceeds mainly through a stepwise hydrogen-abstraction mechanism.

Original languageEnglish
Pages (from-to)9295-9302
Number of pages8
JournalChemistry - A European Journal
Volume25
Issue number39
DOIs
Publication statusPublished - 2019 Jul 11

Keywords

  • C−H activation
  • aromatic compounds
  • dehydrogenation
  • main-group elements
  • reaction mechanisms
  • silylenes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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