Redox catalysis in organic electrosynthesis: basic principles and recent developments
Electroorganic synthesis has become an established, useful, and environmentally benign alternative to classic organic synthesis for the oxidation or the reduction of organic compounds. In this context, the use of redox mediators to achieve indirect processes is attaining increased significance, sinc...
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| Published in | Chemical Society reviews Vol. 43; no. 8; pp. 2492 - 2521 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
England
21.04.2014
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| Subjects | |
| Online Access | Get full text |
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| Summary: | Electroorganic synthesis has become an established, useful, and environmentally benign alternative to classic organic synthesis for the oxidation or the reduction of organic compounds. In this context, the use of redox mediators to achieve indirect processes is attaining increased significance, since it offers many advantages compared to a direct electrolysis. Kinetic inhibitions that are associated with the electron transfer at the electrode/electrolyte interface, for example, can be eliminated and higher or totally different selectivity can be achieved. In many cases, a mediated electron transfer can occur against a potential gradient, meaning that lower potentials are needed, reducing the probability of undesired side-reactions. In addition, the use of electron transfer mediators can help to avoid electrode passivation resulting from polymer film formation on the electrode surface. Although the principle of indirect electrolysis was established many years ago, new, exciting and useful developments continue to be made. In recent years, several new types of redox mediators have been designed and examined, a process that can be accomplished more efficiently and purposefully using modern computational tools. New protocols including, the development of double mediatory systems in biphasic media, enantioselective mediation and heterogeneous electrocatalysis using immobilized mediators have been established. Furthermore, the understanding of mediated electron transfer reaction mechanisms has advanced. This review describes progress in the field of electroorganic synthesis and summarizes recent advances.
The use of redox mediators in electroorganic synthesis has become an important strategy to facilitate reactions and to tune the selectivity. |
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| Bibliography: | R. Daniel Little (Dan) received his BS degree in chemistry and mathematics from the University of Wisconsin-Superior. Graduate studies were carried out under the tutelage of Howard Zimmerman at the University of Wisconsin in Madison. Dan then moved to Yale University where he conducted postdoctoral research with Jerome Berson. Thereafter, he moved west to assume a faculty position at the University of California Santa Barbara. He has held visiting professorships at the University of British Columbia (Canada), the Beijing University of Technology (China), and the University of Regensburg (Germany). He is a member of a number of professional organizations including the American Chemical Society, the Electrochemical Society, the International Society of Electrochemistry, and is a Fellow of the American Association for the Advancement of Science. Robert Francke received his Diploma (equivalent to a MS degree) in chemistry from Bonn University (Germany) in 2008 while studying under the direction of Prof. S. R. Waldvogel. He then moved with Prof. Waldvogel to the University of Mainz (Germany), where he completed his PhD research on fluorinated electrolytes for electrochemical energy storage devices in 2012. With financial support by the Alexander von Humboldt Foundation (Feodor Lynen fellowship) he joined the group of Prof. R. D. Little at the University of California, Santa Barbara as a postdoctoral researcher. His current research focuses on the development and application of new redox catalysts for indirect electroorganic synthesis. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 0306-0012 1460-4744 |
| DOI: | 10.1039/c3cs60464k |