Kajiwara Rikuo, Takamatsu Kazutaka, Hirano Koji, Miura Masahiro
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Org Lett. 2020 Aug 7;22(15):5915-5919. doi: 10.1021/acs.orglett.0c02012. Epub 2020 Jul 16.
A copper-mediated, phenanthroline-directed highly ortho-selective C-H sulfenylation of phenols with diaryl disulfides proceeds to form the corresponding unsymmetrical diaryl sulfides in good yield. The key to success is the introduction of a phenanthroline directing group of the bidentate-chelating nature, which is easily attachable, detachable, and even recyclable. Moreover, the same strategy is applicable to the C-H selenation, giving the diaryl selenides with high efficiency and regioselectivity.
铜介导、菲咯啉导向的酚类与二芳基二硫化物的高度邻位选择性C-H硫醚化反应能够顺利进行，以良好的产率生成相应的不对称二芳基硫醚。成功的关键在于引入具有双齿螯合性质的菲咯啉导向基团，该基团易于连接、去除甚至可回收利用。此外，相同的策略适用于C-H硒化反应，能够高效且区域选择性地生成二芳基硒醚。
