Alkene dicarbofunctionalization by intercepting alkylmetal intermediates

Alkenes serve as important feedstock chemicals for organic synthesis. Functionalization of the two vicinal sites in alkenes with two carbon sourcces is a powerful strategy, which enables us to reduce a multistep process to a short synthetic venture to synthesize complex products from simple starting materials. However, the development of this method is challenging as the alkylmetal species that are generated as reaction intermediates are prone to undergo rapid b-H elimination. In this talk, we will discuss our strategies that address this issue during alkene difunctionalization to create two carbon-carbon bonds across the vicinal sites. Additionally, we will also introduce a new strategy that harnesses the process of b-H elimination to difunctionalize unactivated alkenes at homovicinal sites via the contraction of transient metallacycles. Relevent reaction mechanisms based on radical probes, competition experiments and quantitative kinetic studies will also be discussed.