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C(sp3)-C(sp3) bond formation via electrochemical alkoxylation and subsequent Lewis acid promoted reactions

C(sp3)-C(sp3) bond formation via electrochemical alkoxylation and subsequent Lewis acid promoted reactions

Lopez, Enol, van Melis, Carlo, Martin, Raul, Petti, Alessia, Hoz, Antonio de la, Diaz-Ortiz, Angel, Dobbs, Adrian P. ORCID: 0000-0002-7241-7118, Lam, Kevin ORCID: 0000-0003-1481-9212 and Alcazar, Jesus (2021) C(sp3)-C(sp3) bond formation via electrochemical alkoxylation and subsequent Lewis acid promoted reactions. Advanced Synthesis and Catalysis, 363 (19). pp. 4521-4525. ISSN 1615-4150 (Print), 1615-4169 (Online) (doi:https://doi.org/10.1002/adsc.202100749)

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33408 LAM_C(sp3)-C(sp3)_bond_formation_via_electrochemical_alkoxylation_and_subsequent_Lewis_acid_promoted_reactions_(AAM)_2021.pdf - Accepted Version
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Abstract

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.

Item Type: Article
Uncontrolled Keywords: Electrosynthesis, medchem, sp3
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Faculty / School / Research Centre / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Last Modified: 06 Oct 2021 15:54
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
Selected for GREAT 2019: None
Selected for REF2021: None
URI: http://gala.gre.ac.uk/id/eprint/33408

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