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

Author:

Fukazawa Mizuki1,Takahashi Fumiya1,Kurogi Takashi1,Yorimitsu Hideki1ORCID

Affiliation:

1. Department of Chemistry Graduate School of Science Kyoto University Kyoto, Sakyo-ku 606-8502 Kyoto Japan

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.

Funder

Japan Society for the Promotion of Science

Japan Science and Technology Corporation

Publisher

Wiley

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