Electroreductive Coupling of Aldehydes and Subsequent Pinacol Rearrangement for 1,2‐Disubstituted Ethanones

1,2-Disubstituted ethanones were produced from aldehydes, which involving a electroreductive crossing and a supramolecular pinacol rearrangement.

Abstract

An electrochemical method for the generation of 1,2-diols through the reductive coupling of aldehydes has been developed, and the 1,2-diols were used directly without separation for the pinacol rearrangement process. The electro-organic strategy had mild reaction conditions and avoided the use of reductants. The pinacol rearrangement was controllable to access to the hydride-migrated product 1,2-disubstituted. The key factor in selectivity was the use of macrocyclic compound cucurbit[7]uril, which plays a key role in the interaction with aromatic ring of 1,2-diol. On the basis of experimental results, the mechanism, include the electroreductive coupling and pinacol rearrangement process, was illustrated.

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