Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States.
Org Lett. 2021 Jun 18;23(12):4588-4592. doi: 10.1021/acs.orglett.1c01280. Epub 2021 Jun 1.
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.
本文描述了通过镍催化将硅氧基芳烃转化为硼酸频哪醇酯。与其他惰性 C-O 键的硼化反应不同，该方法能够在没有导向基团的孤立芳环系统中活化硅氧基芳烃的碳氧键。在这些条件下，苄基硅醚的催化官能团化也得以实现。通过利用硅氧基芳烃的正交反应性，可以实现顺序交叉偶联反应，然后可以对其进行后续官能化。
