2021
DOI: 10.1039/d1sc04011a
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Transition metal-catalyzed organic reactions in undivided electrochemical cells

Abstract: Transition metal-catalyzed organic electrochemistry is a rapidly growing research area owing in part of the ability of metal catalysts to alter the selectivity of a given transformation. This conversion...

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Cited by 78 publications
(27 citation statements)
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“…Cross-electrophile coupling generates the same products as cross-coupling but directly from two electrophiles and without the need for stoichiometric metal, in theory . In practice, the use of metal reductants (e.g., Zn, Mn, and Mg) or metal sacrificial anodes has been the most general strategy used for C­(sp 2 )–C­(sp 3 ) bond formation (Scheme ). Applications in industry and academia have almost exclusively generated stoichiometric metal waste (e.g., MnX 2 , ZnX 2 , or boron or silicon waste).…”
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confidence: 99%
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“…Cross-electrophile coupling generates the same products as cross-coupling but directly from two electrophiles and without the need for stoichiometric metal, in theory . In practice, the use of metal reductants (e.g., Zn, Mn, and Mg) or metal sacrificial anodes has been the most general strategy used for C­(sp 2 )–C­(sp 3 ) bond formation (Scheme ). Applications in industry and academia have almost exclusively generated stoichiometric metal waste (e.g., MnX 2 , ZnX 2 , or boron or silicon waste).…”
mentioning
confidence: 99%
“…Besides stoichiometric metal waste, analyses at BMS, ,, Merck, and Pfizer have identified the major issues in scale-up to be heterogeneity/mixing, inconsistency of metallic reductant quality, the possibility of strong exotherms, and reliance on amide solvents (Scheme ). Although progress has been made, no approach has been able to make progress on all of these challenges without introducing new complexities.…”
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confidence: 99%
“…Electrochemical synthesis is increasingly favored by synthetic chemists, due to its unique superiority in the discovery of novel transformations, avoidance of chemical redox agents, 1,2 and independent oxidation and reduction events accomplished in one flask set. 3 On the other hand, the decarboxylative transformation of carboxylic acids has emerged as an attractive strategy to construct C–C and C–X bonds, 4 owing to the ready accessibility and stability of carboxylic acids. 5,6 In particular, decarboxylation of aliphatic carboxylic acids via electrolysis was known as Kolbe electrolysis in 1847, in which carboxylic acids were oxidized and decarboxylated at the anode to produce the corresponding alkyl radicals.…”
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confidence: 99%
“…15 The perfect matches of rate and the electric potential of anodic oxidative decarboxylation and cathodic reduction of electrophiles are required to realize this transformation. 3,16–18 Besides, at least one of the generated intermediates at two separate electrodes should be stable enough to migrate to another electrode surface. 3,19 Finally, the heterogenous electrons transfer from electrodes to substrates making this coupling extremely challenging.…”
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