Sodium-Mediated Reductive C-C Bond Cleavage Assisted by Boryl Groups

Chem Asian J. 2024 Feb 22:e202400100. doi: 10.1002/asia.202400100. Online ahead of print.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.PMID:38385830 | DOI:10.1002/asia.202400100

Source: Chemistry, an Asian Journal - February 22, 2024 Category: Chemistry Authors: Mizuki Fukazawa Fumiya Takahashi Takashi Kurogi Hideki Yorimitsu Source Type: research