Zeng Jialin, Naito Morio, Torigoe Takeru, Yamanaka Masahiro, Kuninobu Yoichiro
Department of Molecular and Material Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan.
Department of Chemistry and Research Center for Smart Molecules, Faculty of Science, Rikkyo University, 3-34-1 Nishi-Ikebukuro, Toshima-ku, Tokyo 171-8501, Japan.
Org Lett. 2020 May 1;22(9):3485-3489. doi: 10.1021/acs.orglett.0c00946. Epub 2020 Apr 23.
A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via -selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH group and the oxygen atom of the boryl ligand, control the -selectivity.
开发了一种简单的铱催化体系，该体系可通过硫代苯甲醚衍生物的选择性C-H硼化反应轻松合成多种2-硼基硫代苯甲醚。引入硼基和甲硫基后，通过钯催化的转化反应将它们进行转化。密度泛函理论计算表明，诸如SCH基团的C-H键与硼基配体的氧原子之间的氢键等弱相互作用控制着选择性。
