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Electrochemical transition-metal-catalyzed C-H bonds functionalization: electricity as clean surrogates of chemical oxidants.
ChemSusChem 2018 October 3
Transition-metal-catalyzed C-H activation attracts tremendous attentions in organic synthetic community because it obviates pre-functionalization of substrates.[1] Significant advances have been dedicated in the past several decades. However, it should be notated that super stoichiometric chemical oxidants, such as copper- or silver-based metal oxidants, benzoquinones (BQ), organic peroxides, potassium persulfate (K2S2O8), hypervalent iodine molecular oxygen (O2) and so on that are required for most of the reactions.[2] The disadvantages associated with above mentioned chemical oxidants, e.g. organic and/or heavy metal pollution, toxicity, highly risk of explosibility, especially because of the large scale usage and high costs limit its application in industry.[3] Thus, development of environmentally benign and user-friendly C-H bonds activation protocols in the absence of chemical oxidants would be urgently desirable. Organic electrosynthesis witnesses the renaissance because of its inherent advantages and unique characters.[4] Many advancements of electrochemistry in organic synthesis[5] as well as in organometallics have been made.[6] Redox reactions involve electron transfer. Therefore, in principle, losing or obtaining electrons on the surface of electrodes can be treated as clean surrogates of chemical redox reagents and thus environmental pollution, high costs, notorious toxicity and high risk of explosibility could be significantly reduced and/or suppressed. The result is fundamentally in line with the purpose of green chemistry. However, successful examples utilizing electricity as the clean surrogates of oxidants in transition-metal-catalyzed C-H activation are very elusive.[6] In order to aid the reader to understand this area, we wish to summarize recent progress in this area until the end of September 2018 in the format of minireview which is built on different transition metals.
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