Metal‐ and Oxidant‐Free Alkenyl C−H/Aromatic C−H Cross‐Coupling Using Electrochemically Generated Iodosulfonium Ions

Ryutaro Hayashi, Akihiro Shimizu, Jonathan Davies, Yu Ishizaki, Chris Willis, Jun-ichi Yoshida

Research output: Contribution to journalArticle (Academic Journal)peer-review

7 Citations (Scopus)
102 Downloads (Pure)

Abstract

A three-step transformation consisting of 1) addition of electrochemically generated iodosulfonium ions to vinylarenes to give (1-aryl-2-iodoethoxy)sulfonium ions, 2) nucleophilic substitution by subsequently added aromatic compounds to give 1,1-diaryl-2-iodoethane, and 3) elimination of HI with a base to give 1,1-diarylethenes was developed. The transformation serves as a powerful metal- and chemical-oxidant-free method for alkenyl C−H/aromatic C−H cross-coupling.

Original languageEnglish
Pages (from-to)12891-12895
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number39
Early online date29 Aug 2018
DOIs
Publication statusPublished - 24 Sep 2018

Structured keywords

  • BCS and TECS CDTs

Keywords

  • benzyl cations
  • oxidation
  • C−H functionalization C−H/C−H cross-coupling
  • electrochemistry
  • C-H/C-H cross coupling

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