Carbon–Carbon Bond Formation via Electron Transfer: Anodic Coupling

Abstract

Electrochemical carbon–carbon coupling: Electrolysis is a facile and green route to dimers of alkyl aromatic compounds, enabling cross‐couplings of phenols and cyclizations of aryl ethers and enol ethers in high selectivities and yields. This Highlight describes the broad scope and simplicity of anodic coupling. HFIP=Hexafluoroisopropanol.

Electrochemical strategies for C–H functionalization and C–N bond formation

“…72 Anodic oxidation processes have been examined by Adams, 73 Eberson 27,74 and Shono, 75 and more recently by Boydston, 76 Chiba, 77 Moeller, [78][79][80][81] and Schäfer. 82,83 Reviews detailing both anodic oxidation and cathodic reduction processes have been summarized by Schäfer, 84,85 Wright 86 and Yoshida. 87 Progress in indirect electrolysis has been reviewed by Nikishin, 42c Steckhan, 42a,b as well as Francke and Little 42d while the synthetic endeavors of using electrochemistry in complex settings have been described by Baran.…”

Electron transfer in polyaromatic hydrocarbons and molecular carbon nanostructures

“…CuCl 2 , FeCl 3 , and by electrochemistry either directly at the electrode, as investigated by Schäfer [58,59] and by Waldvogel [60,14] by using a boron-doped diamond electrode or a molybdenum anode, or indirectly by redox mediators [61]. Recently, electrochemical oxidative coupling of PAHs has been proposed for the synthesis of new materials which are generated by a sequential stepwise coupling of R •+ that finally leads to an insoluble film on the electrode surface.…”

Electrochemical organic reactions: A tutorial review

“…The cathodic reduction and anodic oxidation processes were reviewed in detail by the groups of Yoshida ( Yoshida et al, 2008 ), Schäfer ( Schäfer, 1981 ; Schäfer, 2011 ), Wright ( Sperry and Wright, 2006 ), and Tian ( Chen et al, 2019 ). The anodic electrochemical process was also reviewed by the groups of Eberson ( Eberson and Nyberg, 1973 ; Eberson and Nyberg, 1976 ), Shono ( Shono, 1984 ), Adams ( Adams, 1969 ), Schäfer ( Schafer et al, 2007 ; Schafer, 2014 ), Chiba ( Chiba and Kim, 2009 ), Moeller ( Moeller, 1997 ; Moeller, 2000 ; Moeller, 2016 ; Feng et al, 2017 ), and Boydston ( Ogawa and Boydston, 2015 ). The group of Waldvogel ( Möhle et al, 2018 ; Waldvogel et al, 2018 ; Wiebe et al, 2018 ; Schulz and Waldvogel, 2019 ), Bao Guo Sun ( Yang Q. L. et al, 2018 ), Tian-Sheng Mei ( Ma et al, 2018 ), Zeng ( Jiang et al, 2017 ), Zhang ( Guo et al, 2015 ), and Daugulis ( Daugulis et al, 2015 ) summarized the synthetic attempts at complex structures using electrochemistry.…”