Abstract
We discuss a novel selenium-based reaction mechanism consisting in a selenoxide elimination-triggered enamine hydrolysis. This one-pot model reaction was studied for a set of substrates. Under oxidative conditions, we observed and characterized the formation of primary and secondary amines as elimination products of such compounds, paving the way for a novel strategy to selectively release bioactive molecules. The underlying mechanism was investigated using NMR, mass spectrometry and density functional theory (DFT).
Highlights
From the point of view of the molecular mechanism, the considered oxidationtriggered is distinctive of organoselenium compounds having protons in the
The triggered elimination is distinctive of organoselenium compounds having protons in the βreaction is initiated by the oxidation of the selenium atom to the corresponding position with respect to the chalcogen atom
This process occurs through a syn mechanism selenoxide, a step which can be induced by different agents such as hydrogen peroxide, and promotes the formation of olefins with high trans selectivity [8]
Summary
In the past few decades, the selenoxide elimination reaction has been used to obtain alkenes and has been largely applied in the synthesis of small molecules such as natural products and bioactive compounds [1,2,3,4]. In the presence of oxidants, such as peroxides or other reactive oxygen species (ROS), organoselenium compounds are readily oxidized to selenoxides [5,6,7]. An intramolecular syn elimination occurs in opportune substrates, involving the hydrogen atom in vicinal position with respect to the selenium nucleus. This leads to the formation of the corresponding trans-olefine [8,9,10]
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
