Work

Nickel-Catalyzed Electroreductive Homocoupling of α-Allenyl Electrophiles Provides Direct and Selective Access to [4]-Dendralenes

Year: 2026

Type: article

Abstract: A direct and regioselective route to symmetrical [4]-dendralenes has been developed based on nickel-catalyzed electroreductive homocoupling of α-allenyl electrophiles. The methodology offers the first electrochemical approach to dendralenes and a rare example of nickel-mediated activation of α-allenyl electrophiles. Under mild conditions in an undivided cell, a broad range of α-, β-, and δ-substituted allenyl acetates undergo efficient dimerization to furnish diversely substituted cross-conjugated tetraenes in moderate to good yields. Aryl-substituted substrates display particularly high stereocontrol, generally affording the corresponding dendralenes with excellent preference for the (E,E)-diastereomer. This work introduces a complementary reductive disconnection for [4]-dendralene synthesis and reveals a previously unexplored dimerization manifold of α-allenyl electrophiles.

Source: ACS Organic & Inorganic Au

DOI: 10.1021/acsorginorgau.6c00112

Authors: Camille Beluze, Emmanuel Chefdeville, Didier Bouyssi, Nuno Monteiro, Abderrahmane Amgoune

Institutions: Lyon 1 Université, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,500

Funders: Centre National de la Recherche Scientifique, Université Claude Bernard Lyon 1, Goddard Space Flight Center