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

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).