Electrochemical Synthesis of C(sp 3 )-Rich Heterocycles via Mesolytic Cleavage of Anodically Generated Aromatic Radical Cations.

Autor: Maashi HA; Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building Park Place, Cardiff, CF10 3AT, United Kingdom.; Department of Chemistry, College of Science, University of Bisha, Bisha 61922, Saudi Arabia., Husayni AH; Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building Park Place, Cardiff, CF10 3AT, United Kingdom.; Department of Chemistry, College of Science, Jazan University, Jizan 45142, Saudi Arabia., M K; Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building Park Place, Cardiff, CF10 3AT, United Kingdom., Reid ME; Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building Park Place, Cardiff, CF10 3AT, United Kingdom., Harnedy J; Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building Park Place, Cardiff, CF10 3AT, United Kingdom., Herneman EC; Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building Park Place, Cardiff, CF10 3AT, United Kingdom., Pera-Titus M; Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building Park Place, Cardiff, CF10 3AT, United Kingdom., Morrill LC; Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building Park Place, Cardiff, CF10 3AT, United Kingdom.; Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, United Kingdom.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Oct 25; Vol. 26 (42), pp. 9051-9055. Date of Electronic Publication: 2024 Oct 21.
DOI: 10.1021/acs.orglett.4c03091
Abstrakt: Herein we report an electrochemical deconstructive functionalization approach for the synthesis of C(sp 3 )-rich heterocycles. The reaction proceeds via the mesolytic cleavage of anodically generated aromatic radical cations and the trapping of formed carbocation intermediates with internal nucleophiles. The method has been demonstrated across various arylalcohol substrates to access a diverse range of C(sp 3 )-rich heterocycles including tetrahydrofuran, tetrahydropyran, and pyrrolidine scaffolds (26 examples). The electrochemical method was demonstrated on a 5 mmol scale via single pass continuous flow, which utilized lower supporting electrolyte concentration and exhibited increased productivity in relation to the batch process.
Databáze: MEDLINE
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