Reductive Functionalization of C–C π-Bonds via Alkene Radical Anions

Liam J. Franov; Tayla L. Wilsdon; Anastasios Polyzos

doi:10.1055/a-2678-6468

Synlett, Inhaltsverzeichnis

Synlett
DOI: 10.1055/a-2678-6468

Synpacts

Reductive Functionalization of C–C π-Bonds via Alkene Radical Anions

Authors

Liam J. Franov

¹School of Chemistry, The University of Melbourne, Melbourne, Australia
Tayla L. Wilsdon

¹School of Chemistry, The University of Melbourne, Melbourne, Australia
Anastasios Polyzos

¹School of Chemistry, The University of Melbourne, Melbourne, Australia

²Research Way, CSIRO Manufacturing, Clayton, VIC 3168, Australia

Abstract

Alle Artikel dieser Rubrik

Abstract

Alkene radical anions are powerful yet underutilized intermediates for the construction of C(sp³)–C(sp³) bonds in organic synthesis. This Synpacts article provides an overview of established methods for their generation and functionalization via photoredox catalysis and electrosynthesis. In particular, we highlight our recent development of an electroreductive alkene–aldehyde coupling enabled by rapid alternating polarity. This waveform allows the chemoselective generation of alkene radical anions from vinylarenes and heterocycles and directs their reactivity toward C–C bond formation with alkyl aldehydes to furnish structurally diverse secondary alcohols.

Keywords

Radical anions - Alkenes - Aldehydes - Electrosynthesis - Rapid alternating polarity - Photochemistry

Volltext

Referenzen

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