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.

中文翻译：

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硼通过锌/镍串联催化插入烷基醚键中

轻度的在烷基醚中裂解碳-氧（C-O）键的方法可通过精心设计这些稳固且易于获得的前体来简化化学合成。在这里，我们报道二溴硼烷在镍催化剂和锌还原剂的存在下与烷基醚反应，从而将硼插入到C-O键中。随后的反应性可以影响环醚的氧-氮取代或一碳同系化，并更广泛地简化了生物活性化合物的制备。机理研究揭示了通过锌/镍串联催化的裂解-然后反弹的途径。