Boron insertion into alkyl ether bonds via zinc/nickel tandem catalysis
Published Date: 4/30/2021
Source: phys.org
The carbon-oxygen (C-O) bond in alkyl ethers can be cleaved using mild methods to simplify chemical syntheses by elaborating robust, readily available precursors. In a new report now on Science, Hairong Lyu and a research team in chemistry at the University of Chicago and the University of Pittsburgh, U.S. detailed how dibromoboranes reacted with alkyl ethers in the presence of a nickel (Ni) catalyst and zinc reductant to insert boron into the C-O bond. The subsequent reactivity affected the oxygen-to-nitrogen substitution to streamline the preparation of bioactive compounds more broadly. Using mechanistic studies, the team revealed a cleavage-then-rebound pathway via zinc/nickel tandem catalysis.