Transition-Metal-Free Intermolecular Hydrocarbonation of Styrenes Mediated by NaH/1,10-Phenanthroline

Kanako Nozawa-Kumada, So Onuma, Kanako Ono, Tomohiro Kumagai, Yuki Iwakawa, Katsuhiko Sato, Masanori Shigeno, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

Abstract

A transition-metal-free intermolecular coupling reaction of halocompounds with styrenes in the presence of NaH and 1,10-phenanthroline was developed. This reaction afforded hydrocarbonated products with complete anti-Markovnikov selectivity. The method allows the use of a wide range of halocompounds, including aryl and alkyl halides, and good functional group tolerance. Detailed mechanistic studies indicated that an anilide anion generated in situ by the NaH-mediated reduction of 1,10-phenanthroline works as an electron donor and a hydrogen source.

Original languageEnglish
Article numbere202203143
JournalChemistry - A European Journal
Volume29
Issue number18
DOIs
Publication statusPublished - 2023 Mar 28

Keywords

  • carboradical
  • hydrocarbonation
  • single-electron-transfer
  • sodium hydride
  • styrenes

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