Aryl boronic acid-controlled divergent ring-contraction and ring-opening/isomerization reaction of tert-cyclobutanols enabled by nickel catalysis

Org Biomol Chem. 2023 Aug 16;21(32):6493-6497. doi: 10.1039/d3ob00894k.

Abstract

In this work, we wish to present a nickel-catalyzed divergent ring-contraction and ring-opening/isomerization reaction of tert-cyclobutanols. The key to control these two different reaction pathways is to choose appropriate boronic acid, where the use of phenylboronic acid and pyrimidin-5-ylboronic acid enables a ring-contraction and ring-opening reaction/isomerization, respectively. Both cyclopropyl aryl methanones and 1-aryl butan-1-ones could be selectively obtained.