Nickel-Catalyzed Reductive Alkenylation of Enol Derivatives: A Versatile Tool for Alkene Construction

ConspectusKetone-to-alkene transformations are essential in organic synthesis, and transition-metal-catalyzed cross-coupling reactions involving enol derivatives have become powerful tools to achieve this goal. While substantial progress has been made in nucleophile-electrophile reactions, recent developments in nickel-catalyzed reductive alkenylation reactions have garnered increasing attention. These methods accommodate a broad range of functional groups such as aldehyde, ketone, amide, alcohol, alkyne, heterocycles, and organotin compounds, providing an efficient strategy to access structurally diverse alkenes. This Account primarily highlights the contributions from our laboratory to this growing field while also acknowledging key contributions from other researchers.Our early efforts in this area focused on coupling radical-active substrates, such as α-chloroboronates. This method follows the conventional radical chain mechanism, resulting in facile access to valuable allylboronates. Encouraged by these promising results, we subsequently expanded the substrate scope to encompass radical-inactive compounds. By developing new strategies for controlling cross-selectivity, we enabled the coupling of Csp