Cross-electrophile coupling reactions, in which two electrophiles are coupled in the presence of a reducing agent, are a powerful method for C–C bond formation that can provide orthogonal reactivity to traditional cross-coupling transformations. In particular, nickel-catalyzed cross-electrophile coupling reactions that generate C(sp<sup>2</sup>)–C(sp<sup>3</sup>) bonds have received significant attention over the last decade due to the prevalence of these linkages in pharmaceuticals, and the limitations of current methods to form these bonds. A challenge in developing practical cross-electrophile coupling reactions has been our limited understanding of the reaction mechanism, which for example makes it difficult to rationally reduce the catalyst loading. Unfortunately, it is often challenging to study the mechanism of traditional cross-electrophile coupling reactions due to use of heterogeneous reductants. In this presentation, we describe the development of novel homogeneous organic reductants for cross-electrophile coupling, which have improved our mechanistic understanding of these reactions, and led to improved and new cross electrophile coupling reactions. We demonstrate some of our new methodology on pharmaceutically relevant molecules.

New homogeneous organic reductants for Ni catalyzed cross-electrophile coupling

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