Iwasaki Masayuki, Kaneshika Wataru, Tsuchiya Yuta, Nakajima Kiyohiko, Nishihara Yasushi
Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan.
J Org Chem. 2014 Dec 5;79(23):11330-8. doi: 10.1021/jo502274t. Epub 2014 Nov 21.
A palladium-catalyzed and picolinamide-directed C-H thiolation of naphthylamine derivatives with diaryl disulfides has been developed to provide a convenient route to 8-sulfenyl-1-naphthylamines. The reaction proceeds via a 5-membered palladacycle intermediates to afford the peri-thiolated products exclusively, in contrast to the conventional ortho-functionalization. Moreover, the related direct selenation was also achieved with diaryl diselenides, giving the corresponding selenated products with perfect site-selectivity.
已开发出一种钯催化且由吡啶甲酰胺导向的萘胺衍生物与二芳基二硫化物的C-H硫醇化反应，为制备8-亚磺酰基-1-萘胺提供了一条便捷途径。该反应通过五元钯环中间体进行，与传统的邻位官能化不同，专一性地生成周位硫醇化产物。此外，使用二芳基二硒化物也实现了相关的直接硒化反应，以完美的位点选择性得到相应的硒化产物。
