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Metal‐ and Oxidant‐Free Alkenyl C−H/Aromatic C−H Cross‐Coupling Using Electrochemically Generated Iodosulfonium Ions
Author(s) -
Hayashi Ryutaro,
Shimizu Akihiro,
Davies Jonathan A.,
Ishizaki Yu,
Willis Chris,
Yoshida Junichi
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201807592
Subject(s) - metal , ion , metal ions in aqueous solution , chemistry , coupling (piping) , polymer chemistry , inorganic chemistry , photochemistry , materials science , organic chemistry , metallurgy
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.