Ligand-Enabled Regio- and/or Stereoselective Hydroboration of Alkenes

Alkylboronic acids are widely used in medicinal chemistry, material sciences, and organic synthesis. Accordingly, a large number of methods have been developed for the regio-and stereo-selective synthesis of these structures. Transition-metal-catalyzed hydroboration of alkenes is one of the most convenient and direct methods. However, the stereoselective hydroboration of heteroatom-substituted alkenes and regioselective hydroboration of aliphatic internal alkenes are still challenging. In this account, we emphasize our recent work on ligandenabled transition-metal-catalyzed regio-and/or stereoselective hydroboration of alkenes, including copper-catalyzed asymmetric hydroboration of beta-amidoacrylonitriles, beta-amidoacrylate esters, indole-3-carboxylates, and iridium-catalyzed distal hydroboration of aliphatic internal alkenes. 1 Introduction 2 Copper-Catalyzed Asymmetric Hydroboration of Enamine Derivatives 3 Iridium-Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes 4 Conclusion

Automated summary

Alkylboronic acids are widely used in various fields, and the transition-metal-catalyzed hydroboration of alkenes is a convenient method for their synthesis. However, achieving selective hydroboration of heteroatom-substituted alkenes and regioselective hydroboration of aliphatic internal alkenes remains a challenge. This account highlights recent advancements in ligand-enabled transition-metal-catalyzed regio- and/or stereoselective hydroboration of alkenes.