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Selective Functionalization of Styrenes with Oxygen Using Different Electrode Materials: Olefin Cleavage and Synthesis of Tetrahydrofuran Derivatives
Author(s) -
Imada Yasushi,
Okada Yohei,
Noguchi Keiichi,
Chiba Kazuhiro
Publication year - 2019
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.201809454
Subject(s) - tetrahydrofuran , platinum , chemistry , electrode , electrolysis , electrochemistry , olefin fiber , styrene , surface modification , carbon fibers , inorganic chemistry , photochemistry , polymer chemistry , organic chemistry , materials science , catalysis , copolymer , electrolyte , solvent , composite material , polymer , composite number
Electrode materials can have a significant impact on the course of an electrolysis reaction. Of particular interest is that different electrodes can generate different products from the same substrate. The electrode‐material‐selective transformations of styrene derivatives with molecular oxygen are reported. Platinum electrodes afford carbonyl products via cleavage of olefins, whereas tetrahydrofuran formation is achieved with carbon electrodes. A variety of different styrenes are available for both reactions. Electrolysis allows straightforward and mild chemical conversions that are metal‐ and oxidant‐free. Electrochemical measurements illuminate the different effects of platinum and carbon electrodes on styrenes. The key to the differing reactions is probably that the oxidation potentials of the substrates are lower (higher HOMO energy) on carbon electrodes than on platinum electrodes. The adsorption of the substrates on carbon electrodes can also promote tetrahydrofuran formation.