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June 8, 2026Chemistry - A European Journal0 citationsOpen Access

Nickel‐Catalyzed Reductive Cross‐Coupling of Xanthate Esters With Aryl and Alkenyl Iodides

FVFelix Vöhringer KZKathrin Zwettler DSDmitry I. Sharapa

Key Points

The study aims to explore nickel-catalyzed reductive cross-coupling of xanthate esters with aryl and alkenyl iodides to produce diarylmethanes.
Nickel-catalyzed cross-coupling reactions utilizing xanthate esters with S-allyl substituents and aryl/alkenyl iodides.
Evaluation of reaction tolerance to various functional groups.
Mechanistic studies investigating radical generation via single electron transfer by Ni(I).
Higher yields were obtained with S-allyl xanthate esters compared to S-Me xanthate esters.
The reaction effectively converted xanthate esters derived from pharmaceuticals to diarylmethanes.
The electronic properties of the reaction partners significantly impacted the reaction outcomes.

Abstract

ABSTRACT We report a nickel‐catalyzed reductive cross‐coupling of xanthate esters and aryl and alkenyl iodides. Utilizing xanthate esters with an S ‐allyl substituent leads to higher yields compared to the more commonly used S ‐Me xanthate esters. The reaction is tolerant toward a wide array of functional groups and allows for the conversion of xanthate esters derived from pharmaceuticals to diarylmethanes. Electronic properties of the reaction partners have a strong influence on the reaction. Mechanistic investigations revealed that the benzylic radical is generated from the xanthate ester, presumably by single electron transfer by Ni(I).

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