Organic Electrosynthesis

Organic electrosynthesis: Electrosynthesis is naturally a huge topic within the field of electrochemistry. Although it has an extensive history, it has recently seen a new era of growth and is now largely considered its own field rather than simply a subdiscipline. This Special Issue highlights the latest research in this exciting field. Since Kolbe′s pioneering work in the middle of the nineteenth century,1 electrosynthesis has become known as a useful tool to achieve a variety of organic transformations.2 With countless applications on a laboratory scale and some industrial processes, it can be considered a versatile and mature discipline. Spurred on by the establishment of the adiponitrile process by Manuel Baizer in the 1960s (the most successful electroorganic process to date),3 the field experienced a peak phase through the 1970s and 1980s, but then gradually fell out of the focus of academic researchers. One reason for this is certainly the failure to sustainably integrate electrosynthesis into university teaching. Today it is, therefore, not surprising that, for most chemists, the term “electrochemistry” is associated with their experience from courses in physical and analytical chemistry. Simultaneously, electrosynthesis has not yet made its way into organic chemistry textbooks and has thereby failed to become an integral part of the repertoire of preparative chemists. As a consequence, for many years it was practiced and appreciated by a rather small scientific community. Very recently, the methodology has experienced a resurrection, which is, in part, driven by the increasing importance of intermittent renewable energy sources and the idea of using local and temporary excesses of electric energy for the production of value-added chemicals. A second driving force behind this renaissance is the ongoing quest for new sustainable synthetic methods. What can be more promising, for example, than avoiding reagent waste by using “clean” electricity? However, the sole reason given by sustainability and energy management does not do justice to the versatility and possibilities of the methodology. In fact, another outstanding feature is the possibility of making unique reactive intermediates accessible in a controlled and predictable manner. Organic electrosynthesis is a rich and continually evolving field that offers numerous opportunities to synthetic chemists who are willing to step out of their comfort zone, as witnessed by the research papers and topical reviews of this Special Issue of ChemElectroChem. A significant share of these contributions deals with the generation of unique reactive intermediates and, concomitantly, with the development of new synthetic methods. As highlighted by several Reviews and Minireviews, the application of electrochemistry to new synthetic challenges, such as the synthesis of certain complex molecules or to the conversion of renewable raw materials, prove to be promising and fruitful areas. Other contributions focus upon the exploration of homogeneous and heterogeneous electrocatalysts for electrosynthetic applications, a sub-discipline with plenty of room for further work. Until now, a great number of electrosynthetic reactions were exclusively carried out in batch mode, whereas flow electrosynthesis allows for efficient upscaling and minimization of both supporting electrolyte load and solvent consumption. Further opportunities lie in the investigation of electroorganic reaction mechanisms, especially since voltammetric approaches and spectroelectrochemical methods have evolved significantly in recent decades and have become available on a broader basis. Other contributions highlight the opportunities at the interface between electrochemistry and materials (polymers) as well as in the fields of innovative electrode materials and electrolyte concepts. In short, the possibilities to advance organic synthesis with electrochemical methods are great and, as this Special Issue demonstrates, the synthetic community has already started to unlock this potential. Apart from the wealth of ideas and possible research projects, it is also important to keep an eye on what needs to be done to sustainably establish electrochemistry as a part of organic synthesis. This will certainly involve increased teaching efforts, including the routine incorporation of the chemistry into basic and advanced textbooks, as well as a closer exchange with industrial chemists. After all, the future of this technology depends crucially on well-trained young scientists and on people outside the academic environment recognizing its great value and potential. Robert Francke studied chemistry at Bonn University (Germany) and Alicante University (Spain). In 2008, he received his diploma degree (equivalent to a M.S. degree) from Bonn University, where he subsequently started working on his dissertation under the direction of Prof. S. R. Waldvogel. After relocation of the Waldvogel Group, he completed his dissertation on fluorinated electrolytes for electrochemical energy storage devices at Mainz University (Germany) in 2012. Funded by the Alexander von Humboldt Foundation (Feodor Lynen Fellowship), he then joined the group of Prof. R. D. Little at the University of California, Santa Barbara (USA), where he entered the field of organic electrosynthesis. In 2014, he returned to Germany to start his independent career at Rostock University as a Liebig Fellow (Fonds der Chemischen Industrie). Aside from developing new electrosyntheses and sustainable electrolyte concepts, his research group is currently active at the intersection between catalysis and electrochemistry. Shinsuke Inagi received his PhD from Kyoto University (Japan) in 2007 under the direction of Prof. Yoshiki Chujo. After a postdoctoral research fellowship (Research Fellowship for Young Scientists of the Japan Society for the Promotion of Science, JSPS) at Kyoto University, he joined the group of Prof. Toshio Fuchigami as an Assistant Professor at Tokyo Institute of Technology (Japan) in 2007. He was promoted to Lecturer in 2011, then to Associate Professor in 2015. He has concurrently been a PRESTO researcher of Japan Science and Technology Agency (JST) since 2018. His current research interests include electrosynthesis of functional organic/polymeric materials. He is the recipient of the Tajima Prize of the International Society of Electrochemistry (ISE) in 2019. R. Daniel Little (Dan) studied chemistry and mathematics in the USA at the University of Wisconsin in Superior, the University of South Dakota (two summers sponsored by the National Science Foundation), and Argonne National Laboratory (one semester). Graduate work was accomplished in the group of Howard Zimmerman at the University of Wisconsin, and postdoctoral studies with Jerome Berson at Yale. Other than sabbaticals at the University of British Columbia (Canada), the Beijing Institute of Technology (China), and the University of Regensburg (Germany), Dan has spent his entire academic career at the University of California Santa Barbara (UCSB, USA). There he has served in many capacities including Department Chair. Dan has been interested in electrochemistry for many years and has worked on the development and mechanistic understanding of a number of well-known electrochemical transformations. He remains keenly interested in electron transfer and mediated processes carried out both electrochemically and photochemically. He is a past recipient of the Heyrovsky Prize from the International Society of Electrochemistry (ISE).

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