Xiao Qian, Zhang Hong, Li Jing-Hong, Jian Jing-Xin, Tong Qing-Xiao, Zhong Jian-Ji
Department of Chemistry, Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, and Chemistry and Chemical Engineering Laboratory of Guangdong Province, Shantou University, Shantou, Guangdong 515063, P. R. China.
School of Chemistry and Environmental Engineering, Hanshan Normal University, Chaozhou, Guangdong 521041, P. R. China.
Org Lett. 2021 May 7;23(9):3604-3609. doi: 10.1021/acs.orglett.1c00999. Epub 2021 Apr 12.
In contrast with the well-developed radical thiol-ene reaction to access anti-Markovnikov-type products, the research on the catalytic Markovnikov-selective hydrothiolation of alkenes is very restricted. Because of the catalyst poisoning of metal catalysts by organosulfur compounds, limited examples of transition-metal-catalyzed thiol-ene reactions have been reported. However, in this work, a directing-group-assisted hydrothiolation of styrenes with thiols by photoredox/cobalt catalysis is found to proceed smoothly to afford Markovnikov-type sulfides with excellent regioselectivity.
与用于制备反马氏规则型产物的成熟的自由基硫醇-烯反应相比，关于烯烃的催化马氏规则选择性氢硫基化反应的研究非常有限。由于有机硫化合物会使金属催化剂中毒，因此报道的过渡金属催化硫醇-烯反应的实例有限。然而，在这项工作中，发现通过光氧化还原/钴催化，在导向基团辅助下苯乙烯与硫醇的氢硫基化反应能够顺利进行，以优异的区域选择性得到马氏规则型硫化物。
