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Synlett
DOI: 10.1055/a-2678-6468
DOI: 10.1055/a-2678-6468
Synpacts
Reductive Functionalization of C–C π-Bonds via Alkene Radical Anions
A.P. acknowledges the ARC (FT220100345, DP210100025) for the generous financial support. L.J.F. and T.L.W gratefully acknowledge the Australian Commonwealth Government and the University of Melbourne for the Research Training Program (RTP) Scholarship.
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 - PhotochemistryPublication History
Received: 04 June 2025
Accepted after revision: 13 July 2025
Article published online:
20 August 2025
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During the revision of this manuscript, Yu, Zhang and co-workers also reported a metallophotoredox-catalysed alkynylcarboxylation of alkenes with CO2 and alkynes: