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Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C–O Bond Activation

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posted on 2021-06-01, 14:04 authored by Wesley L. Pein, Eric M. Wiensch, John Montgomery
The conversion of silyloxyarenes to boronic acid pinacol esters via nickel catalysis is described. In contrast to other borylation protocols of inert C–O bonds, the method is competent in activating the carbon–oxygen bond of silyloxyarenes in isolated aromatic systems lacking a directing group. The catalytic functionalization of benzyl silyl ethers was also achieved under these conditions. Sequential cross-coupling reactions were achieved by leveraging the orthogonal reactivity of silyloxyarenes, which could then be functionalized subsequently.