hydrostibination

Hydrostibination is the addition of a Sb–H bond across a carbon–carbon multiple bond, yielding new C–H and C–Sb bonds and producing organostibane products. The reaction is most commonly applied to alkenes and alkynes using antimony hydride reagents such as R3SbH or related stibanes. From alkenes it furnishes alkylstibanes, while from alkynes it furnishes vinylstibanes. The process is conceptually analogous to hydroboration or hydrosilylation, providing a method to install a C–Sb bond in a single step.

Reaction mechanisms vary with substrate and conditions. Some hydrostibinations proceed by concerted, stereoselective syn-addition across the unsaturation; others proceed via radical pathways under photochemical or radical-initiated conditions. Regio- and stereochemical outcomes depend on substrate, reagent, and reaction environment.

Scope and safety: Demonstrated for a range of terminal and internal alkenes and alkynes, though substrate scope can be limited and reagents may be air- and moisture-sensitive. Antimony compounds are toxic, requiring appropriate safety precautions and handling.

Applications: The primary utility is the construction of C–Sb bonds, providing versatile handles for further transformations such as oxidation, substitution, or cross-coupling to access diverse hydrocarbon or functionalized products.