Synthesis of α-Vinylboron Compounds via the Palladium-Catalyzed Regioselective Mizoroki-Heck Reaction

Abstract

Developing more efficient and robust reaction methodologies is one of the paramount objectives for synthetic chemists. The creation of novel reactions provides chemists with access to a diverse range of molecular structures, which also advances the development of related scientific fields. A notable example is the metal-catalyzed cross-coupling reaction to form carbon-carbon and carbon-heteroatom bonds, which considered as one of the most significant advancements from the last half century of synthetic organic chemistry, has emerged as the most extensively employed reaction class in medicinal chemistry to synthesize pharmaceutical compounds. In the Newman lab, the research interests are based on methodology development with transition-metal catalysts and design of ligands. Chapter 1 gives an overview of cross-couplings, Mizoroki-Heck reactions, and the development of 1,5-diaza-3,7-diphosphacyclooctane (P₂N₂) ligands in metal-catalyzed organic transformations. Chapter 2 describes our efforts in developing of highly regioselective Mizoroki-Heck reactions for the synthesis of α-vinylboron compounds by employing Pd/P₂N₂ catalyst system. This reaction aims to offer a rapid and reliable method for obtaining α-vinylboron compounds, recognized as valuable building blocks in organic synthesis.