VinylBPin

VinylBPin is a term used to describe a vinylboronate ester in which a vinyl group is attached to a pinacol boronate (BPin) moiety. It is a class of organoboron compounds often written as vinyl–BPin. These compounds are favored for their stability and compatibility with common organic solvents and reaction conditions, making them useful building blocks in modern synthetic chemistry.

Chemically, vinylBPin refers to vinyl boronate esters with the pinacol protecting group. The typical representation is a vinyl carbon–carbon double bond linked to the BPin unit (for example, CH2=CH–BPin or related substitutions on the vinyl moiety). VinylBPin compounds can be prepared by methods such as hydroboration of alkynes with pinacolborane or by nickel- or palladium-catalyzed borylation of vinyl halides or vinyl triflates. They are viewed as stable, isolable sources of vinyl boron species suitable for cross-coupling applications.

Applications and reactivity center on vinylBPin as a nucleophilic vinyl partner in cross-coupling reactions, especially Suzuki–Miyaura couplings. After transmetalation, the vinyl group is transferred to a palladium complex and coupled with aryl or vinyl partners to form new carbon–carbon bonds. Their air- and moisture-stable nature often offers practical advantages over more labile boronic acids, enabling straightforward purification and storage. They are widely used in the synthesis of complex, functionally diverse vinyl arenes and other vinyl-containing motifs, including in medicinal chemistry and material science contexts.