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Mn-Mediated Alpha-Radical Addition of Carbonyls to Olefins: Systematic Study, Scope, and Electrocatalysis

Abstract : A systematic study of the manganese-mediated alpha-radical addition of carbonyl groups to olefins is presented. After an in-depth investigation of the parameters that govern the reaction, a first round of optimization allowed the development of a unified stoichiometric set of conditions which was subsequently assessed during the exploration of the scope. Due to observed limitations, the knowledge accumulated during the initial study was reengaged to quickly optimize promising substrates that were so far inaccessible under previously reported conditions. Altogether these results led to the creation of a predictive model based on the pKa of the carbonyl compound and both the substitution and geometry of the alkene coupling partner. Finally, a departure from the use of stoichiometric manganese was enabled through the development of a robust and practical electrocatalytic version of the reaction.
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https://hal-cnrs.archives-ouvertes.fr/hal-03795372
Contributor : Julien VANTOUROUT Connect in order to contact the contributor
Submitted on : Friday, November 25, 2022 - 10:18:42 AM
Last modification on : Tuesday, November 29, 2022 - 9:25:19 AM

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Sylvain Charvet, Maurice Médebielle, Julien Vantourout. Mn-Mediated Alpha-Radical Addition of Carbonyls to Olefins: Systematic Study, Scope, and Electrocatalysis. 2022. ⟨hal-03795372⟩

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