Redox Coupling of Arylmagnesium Reagents with Gem-Dichloroalkanes Enables C(sp²)−C(sp³)/C(sp³)−C(sp³) Bond Formations

Dedication

Dedicated to Prof. Paul Knochel on the occasion of his 70th birthday.

Abstract

The oxidative homocoupling of organomagnesium reagents has been well studied, but the sacrificial oxidants used in these reactions are usually not incorporated into the coupling products. Herein, we report a chromium- or manganese-catalyzed coupling reaction of arylmagnesium reagents with gem-dichloroalkanes (RR′CCl₂), in which RR′CCl₂ serves as both oxidant and coupling reagent. This catalytic redox coupling reaction enables the convenient synthesis of various functionalized dibenzyl derivatives via successive C(sp²)−C(sp³)/C(sp³)−C(sp³) bond formations. A radical-involved mechanism is proposed and experimentally evidenced.

Keywords

Coupling - Organomagnesium reagent - Chromium - Manganese - gem-Dichloroalkane - Dibenzyl - Carbon–carbon bond formation

Publikationsverlauf

Eingereicht: 31. August 2025

Angenommen nach Revision: 01. Oktober 2025

Accepted Manuscript online:
01. Oktober 2025

Artikel online veröffentlicht:
31. Oktober 2025

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