Yttrium-Mediated Conversion of Vinyl Grignard Reagent to a 1,2-Dimetalated Ethane and Its Synthetic Application

摘要

Among the lanthanide reagents used to mediate organic reactions, yttrium reagents are used for hydroyttration, hydrosilylation, and hydroamination of alkenes and alkynes and show a preference for interaction with carbon-carbon multiple bonds. Here we report that an yttrium reagent can react even with a metalated alkene such as a vinyl Grignard reagent, leading to a new method of generating 1,2-dimetalated ethane 1 (Scheme 1). As there are still limitations in the practical generation of 1,2-dimetalated ethane, a fundamental dicarbanionic species and a versatile conjunctive reagent, we also demonstrate some synthetic applications of 1 according to Scheme 1.