Boron insertion into alkyl ether bonds via zinc/nickel tandem catalysis.
basic_science · Level V
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- Record sourced from PubMed, PMID 33833121.
- Also identified by DOI 10.1126/science.abg5526.
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Abstract
Mild methods to cleave the carbon-oxygen (C-O) bond in alkyl ethers could simplify chemical syntheses through the elaboration of these robust, readily available precursors. Here we report that dibromoboranes react with alkyl ethers in the presence of a nickel catalyst and zinc reductant to insert boron into the C-O bond. Subsequent reactivity can effect oxygen-to-nitrogen substitution or one-carbon homologation of cyclic ethers and more broadly streamline preparation of bioactive compounds. Mechanistic studies reveal a cleavage-then-rebound pathway via zinc/nickel tandem catalysis.