4.8 Review

Electrochemical Oxidation Induced Selective C-C Bond Cleavage

Journal

CHEMICAL REVIEWS
Volume 121, Issue 1, Pages 485-505

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.chemrev.0c00335

Keywords

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Funding

  1. National Natural Science Foundation of China [21632001, 21772002, 81821004]
  2. Drug Innovation Major Project [2018ZX09711-001]
  3. Peking University Health Science Center [BMU20160541]
  4. Open Research Fund of Shanghai Key Laboratory of Green Chemistry and Chemical Processes
  5. Natural Science Basic Research Program of Shaanxi [2018JQ2063]

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Selective C-C bond cleavage using electrochemical methods has been identified as a sustainable and scalable strategy that shows potential in replacing chemical reagents with electricity. Progress in this area has been made, with more examples of C-C bond cleavage via different maneuvers being developed recently, showcasing the exciting potential of electrochemical synthesis.
Selective C-C bond cleavage under mild conditions can serve as a valuable tool for organic syntheses and macromolecular degradation. However, the conventional chemical methods have largely involved the use of noble transition-metal catalysts as well as the stoichiometric and perhaps environmentally unfriendly oxidants, compromising the overall sustainable nature of C-C transformation chemistry. In this regard, electrochemical C-C bond cleavage has been identified as a sustainable and scalable strategy that employs electricity to replace byproduct-generating chemical reagents. To date, the progress made in this area has mainly relied on Kolbe electrolysis and related processes. Encouragingly, more and more examples of the cleavage of C-C bonds via other maneuvers have recently been developed. This review provides an overview on the most recent and significant developments in electrochemically oxidative selective C-C bond cleavage, with an emphasis on both synthetic outcomes and reaction mechanisms, and it showcases the innate advantages and exciting potentials of electrochemical synthesis.

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