1-Phenylvinylboronic acid is useful for various coupling reactions, including Liebeskind-Srogl cross-coupling, arylboronic acid homocoupling, boronate building block iterative cross-coupling, and Suzuki-Miyaura cross-coupling. 1-Phenylvinylboronic acid is also used as a reactant for alkyne halogenation, hydroxyphenyl styrene enantioselective hydrogenation, and samarium diiodide-mediated cyclization for synthesis of substituted benznnulated cyclooctanol derivatives.