Interestingly, β-nitrostyrenes, typically bench stable compounds, are highly promising cross-coupling partners, due to their excellent availability and well understood reactivity. In this review, we report on the discovery and advancements, in the field of stereoselective, denitrative cross-couplings of β-nitrostyrenes with miscellaneous organic reagents. The rapidly expanding field offers alternative access to a broad range of functionalized alkenes, including β-alkylated styrenes, chalcones, stilbenes, cinnamic acids, and conjugated sulfones and phosphonates. The most important mechanistic pathways are briefly discussed, to familiarize readers with the elementary reactions occurring during the coupling.

A stereoselective, denitrative cross-coupling of β-nitrostyrenes with N-alkylpyridinium salts for the preparation of functionalized styrenes has been developed. The visible-light-induced reaction proceeds without any catalyst at ambient temperature. Broad in scope and tolerant to multiple functional groups, the moderately yielding transformation is orthogonal to several traditional metal-catalyzed cross-couplings.