C( sp 3 )−C( sp 3 ) Bond Formation via Electrochemical Alkoxylation and Subsequent Lewis Acid Promoted Reactions

Autor:	Jesús Alcázar, Adrian P. Dobbs, Antonio de la Hoz, Raúl Martín, Angel Díaz-Ortiz, Alessia Petti, Enol López, Carlo G. W. van Melis, Kevin Lam
Rok vydání:	2021
Předmět:	Chemistry Iminium General Chemistry Flow chemistry Alkylation Q1 Electrochemistry Combinatorial chemistry chemistry.chemical_compound Reagent Aminal QD Lewis acids and bases Derivatization
Zdroj:	Advanced Synthesis & Catalysis. 363:4521-4525
ISSN:	1615-4169 1615-4150
Popis:	A new and practical 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 new 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 new methodology was applied to derivatization of peptides and an API.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1bc6b0b955dd0ec49f42bcae15c017e4 https://doi.org/10.1002/adsc.202100749 Zobrazit plný text záznamu Plný text ve formátu PDF