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

Rong Chen; Wenhua Yu; Shaopeng Wei; Feng Ouyang; Guipeng Yu; Baosheng Wei

doi:10.1055/a-2715-0392

Synthesis, Inhaltsverzeichnis

Synthesis
DOI: 10.1055/a-2715-0392

Paper

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

Authors

Rong Chen

¹College of Chemistry and Chemical Engineering, Central South University, Changsha, China (Ringgold ID: RIN12570)
Wenhua Yu

¹College of Chemistry and Chemical Engineering, Central South University, Changsha, China (Ringgold ID: RIN12570)
Shaopeng Wei

¹College of Chemistry and Chemical Engineering, Central South University, Changsha, China (Ringgold ID: RIN12570)
Feng Ouyang

¹College of Chemistry and Chemical Engineering, Central South University, Changsha, China (Ringgold ID: RIN12570)
Guipeng Yu

¹College of Chemistry and Chemical Engineering, Central South University, Changsha, China (Ringgold ID: RIN12570)
Baosheng Wei

¹College of Chemistry and Chemical Engineering, Central South University, Changsha, China (Ringgold ID: RIN12570)

Abstract

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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.

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