Revisiting the Chemistry of Vinylpyrazoles: Properties, Synthesis, and Reactivity

Vinylpyrazoles, also known as pyrazolyl olefins, are interesting motifs in organic chemistry but have been overlooked. This review describes the properties and synthetic routes of vinylpyrazoles and highlights their versatility as building blocks for the construction of more complex organic molecules. Concerning the reactivity of vinylpyrazoles, the topics surveyed herein include their use in cycloaddition reactions, free-radical polymerizations, halogenation and hydrohalogenation reactions, and more recently in transition-metal-catalyzed reactions, among other transformations. The current state of the art about vinylpyrazoles is presented with an eye to future developments regarding the chemistry of these interesting compounds. Styrylpyrazoles were not considered in this review, as they were the subject of a previous review article published in 2020.

Automated summary

This review describes the properties, synthetic approaches, and versatile applications of vinylpyrazoles as building blocks in organic chemistry. It covers their reactivity in various reactions, including cycloadditions, polymerizations, halogenation, hydrohalogenation, and transition-metal-catalyzed reactions. The review provides an overview of the current state of the art and future prospects in the chemistry of vinylpyrazoles.