Sodium‐Mediated Reductive C−C Bond Cleavage Assisted by Boryl Groups

Abstract

AbstractIn contrast to the well‐established oxidative C=C double bond cleavage to give the corresponding carbonyl compounds, little is known about reductive C=C double bond cleavage. Here we report that C−C single bond cleavage in 1,2‐diaryl‐1,2‐diborylethanes proceeds by reduction with sodium metal to yield α‐boryl benzylsodium species. In combination with our previous reductive diboration of stilbenes, the overall transformation represents reductive cleavage of the C=C double bonds of stilbene to yield α‐boryl‐α‐sodiated toluenes. This reductive two‐step C=C double bond cleavage is applicable to ring‐opening or ring‐expansion reactions of polycyclic aromatic hydrocarbons.