C(sp3)−C(sp3) Bond Formation via Electrochemical Alkoxylation and Subsequent Lewis Acid Promoted Reactions
A two‐step transition metal‐free methodology for the C(sp3)−C(sp3) functionalisation of saturated N‐heterocyclic systems is disclosed. First, aminal derivatives are generated through the anodic oxidation of readily accessible carboxylic acids. Then, in the presence of BF3 ⋅ OEt2, iminium ions are un...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2021-10, Vol.363 (19), p.4521-4525 |
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| container_issue | 19 |
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| container_title | Advanced synthesis & catalysis |
| container_volume | 363 |
| creator | López, Enol Melis, Carlo Martín, Raúl Petti, Alessia Hoz, Antonio Díaz‐Ortíz, Ángel Dobbs, Adrian P. Lam, Kevin Alcázar, Jesús |
| description | A two‐step transition metal‐free methodology for the C(sp3)−C(sp3) functionalisation of saturated N‐heterocyclic systems is disclosed. First, aminal derivatives are generated through the anodic oxidation of readily accessible carboxylic acids. Then, in the presence of BF3 ⋅ OEt2, iminium ions are unmasked and rapidly alkylated by organozinc reagents under flow conditions. Secondary, tertiary and quaternary carbon centers have been successfully assembled using this methodology. Such an approach is especially relevant to drug discovery since it increases C(sp3)‐functionalities rapidly within a molecular framework. As proof of concept, our methodology was applied to derivatization of peptides and an API. |
| doi_str_mv | 10.1002/adsc.202100749 |
| format | Article |
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First, aminal derivatives are generated through the anodic oxidation of readily accessible carboxylic acids. Then, in the presence of BF3 ⋅ OEt2, iminium ions are unmasked and rapidly alkylated by organozinc reagents under flow conditions. Secondary, tertiary and quaternary carbon centers have been successfully assembled using this methodology. Such an approach is especially relevant to drug discovery since it increases C(sp3)‐functionalities rapidly within a molecular framework. 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| ispartof | Advanced synthesis & catalysis, 2021-10, Vol.363 (19), p.4521-4525 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkylation Anodizing Carboxylic acids Chemical reactions Drug discovery Electrochemistry Flow chemistry Lewis acid Methodology Organozinc reagents Oxidation Peptides Reagents Transition metals Transition-metal free |
| title | C(sp3)−C(sp3) Bond Formation via Electrochemical Alkoxylation and Subsequent Lewis Acid Promoted Reactions |
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