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

Ryutaro Hayashi; Akihiro Shimizu; Jonathan A Davies; Yu Ishizaki; Chris Willis; Jun-Ichi Yoshida

doi:10.1002/anie.201807592

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

Angew Chem Int Ed Engl. 2018 Sep 24;57(39):12891-12895. doi: 10.1002/anie.201807592. Epub 2018 Aug 29.

Authors

Ryutaro Hayashi¹, Akihiro Shimizu¹, Jonathan A Davies², Yu Ishizaki¹, Chris Willis², Jun-Ichi Yoshida³

Affiliations

¹ Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
² School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK.
³ National Institute of Technology, Suzuka College, Suzuka, Mie, 510-0294, Japan.

PMID: 30156746
DOI: 10.1002/anie.201807592

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.

Keywords: C−H functionalization; C−H/C−H cross-coupling; benzyl cations; electrochemistry; oxidation.

Abstract

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