State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, PR China.
Org Lett. 2012 Oct 19;14(20):5362-5. doi: 10.1021/ol302562a. Epub 2012 Oct 2.
An efficient synthesis of 2- or 4-iododibenzofurans through CuI-mediated sequential iodination/cycloetherification of two aromatic C-H bonds in o-arylphenols has been developed. Both the preexisting electron-withdrawing groups (NO(2), CN, and CHO) and the newly introduced iodide are readily modified for a focused dibenzofuran library synthesis. Mechanistic studies and DFT calculations suggest that a Cu(III)-mediated rate-limiting C-H activation step is involved in cycloetherification.
通过 CuI 介导的邻芳基苯酚中两个芳环 C-H 键的顺序碘化/环醚化反应，高效合成了 2-或 4-碘二苯并呋喃。先前存在的吸电子基团（NO2、CN 和 CHO）和新引入的碘化物都很容易进行修饰，以用于有针对性的二苯并呋喃文库合成。机理研究和 DFT 计算表明，环醚化反应涉及 Cu(III)介导的限速 C-H 活化步骤。
