Ligand-Free Iron-Catalyzed Regioselectivity-Controlled Hydroboration of Aliphatic Terminal Alkenes was written by Su, Wei;Qiao, Rui-Xiao;Jiang, Yuan-Ye;Zhen, Xiao-Li;Tian, Xia;Han, Jian-Rong;Fan, Shi-Ming;Cheng, Qiushi;Liu, Shouxin. And the article was included in ACS Catalysis in 2020.COA of Formula: C12H15NO3S This article mentions the following:
The control of regioselectivities has been recognized as the elementary issue for alkene hydroboration. Despite considerable progress, the specificity of alkene substrates or the adjustment of ligands was necessary for specific regioselectivities, which restrict the universality and practicability. Herein, we report a ligand-free iron-catalyzed regiodivergent hydroboration of aliphatic terminal alkenes that obtains both Markovnikov and anti-Markovnikov hydroboration products in high regioselectivities. Notably, solvents and bases were shown to be crucial factors influencing the regioselectivities and further studies suggested that the iron-boron alkoxide ate complex is the key intermediate that determines the unusual Markovnikov regioselectivity. Terminal alkenes with diverse structures (monosubstituted and 1,1-disubstituted, open-chain and exocyclic) underwent the transformation smoothly. The reaction does not require the addition of auxiliary ligands and it can be performed on a gram scale, thus providing an efficient and sustainable method for the synthesis of primary, secondary, and tertiary alkyl borates. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9COA of Formula: C12H15NO3S).
1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.COA of Formula: C12H15NO3S
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem