C(sp²)–C(sp³) Suzuki–Miyaura Cross-Coupling Using gem-Bis(boronates)

A strategy utilizing gem-bis(boronates) as a stable and easily accessible surrogate for the analogous monoboronate and their efficient use in Suzuki-Miyaura cross-couplings to access the highly interesting 1,2-diaryl ethane motif is described. The general reactivity of gem-bis(boronates) and its advantages over monoboronate are demonstrated by a broad substrate scope and minimal β-hydride elimination side product formation. Cusparine, an antituberculosis natural product, was synthesized via this method with a shortened route, demonstrating its brevity, effectiveness, and scalability.