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

Angewandte Chemie
Ryutaro HayashiJun-ichi Yoshida

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.

References

Sep 2, 1994·Journal of Medicinal Chemistry·M F BoehmR A Heyman
Jul 4, 2003·The Journal of Organic Chemistry·Jean-Michel BechtCharles Mioskowski
Jun 23, 2006·Chemical Society Reviews·Jeffrey B Sperry, Dennis L Wright
Dec 28, 2007·Accounts of Chemical Research·Paul A WenderThomas H Pillow
Jun 21, 2008·Chemical Reviews·Jun-ichi YoshidaAiichiro Nagaki
Mar 12, 2011·Chemical Reviews·Jean Le Bras, Jacques Muzart
Oct 1, 2011·Bioorganic & Medicinal Chemistry·Alexander L RuchelmanGeorge W Muller
Aug 14, 2012·The Journal of Organic Chemistry·Hiroko AisoFumitoshi Kakiuchi
Jul 12, 2013·The Journal of Organic Chemistry·Roderick C JonesDonal F O'Shea
Oct 12, 2013·Journal of the American Chemical Society·Yosuke AshikariJun-ichi Yoshida
Feb 24, 2015·Chemical Communications : Chem Comm·Toshihiro AraiMahito Atobe
Aug 5, 2015·Chemistry : a European Journal·Rishikesh NarayanAndrey P Antonchick
Jun 10, 2016·ACS Central Science·Evan J HornPhil S Baran
Jun 25, 2016·Journal of the American Chemical Society·Ryutaro HayashiJun-Ichi Yoshida
Dec 1, 1969·Journal of the American Chemical Society·Y FujiwaraS Teranishi
Oct 7, 2016·Chemical Communications : Chem Comm·Soumitra AgastiDebabrata Maiti
Oct 30, 2016·Chemistry : a European Journal·Ryutaro HayashiJun-Ichi Yoshida
Mar 3, 2017·Angewandte Chemie·Lara SchulzSiegfried R Waldvogel
Oct 28, 2017·Chemical Reviews·Jun-Ichi YoshidaRyutaro Hayashi

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Citations

Aug 16, 2019·Chemistry : a European Journal·Yosuke AshikariAiichiro Nagaki
Apr 10, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Fumitoshi Kakiuchi, Takuya Kochi

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