Abstract
The reaction mechanism and regioselectivity for the gold(I)-catalyzed hydroamination reaction of terminal alkenes are analyzed by means of density functional theory (DFT) calculations. The influence of the nature of the olefin as well as the ligand present in the gold(I) catalyst on the regioselectivity is investigated. The anti-Markovnikov addition is preferred for some alkenes, particularly those having cyclopropyl or good electron-withdrawing groups in their structures. The regioselectivity of the process is quantitatively analyzed with the help of state-of-the-art computational methods, namely, the activation strain model (ASM) of reactivity and natural orbitals for chemical valence (NOCV) method. It is found that the back-bonding interactions in the initially formed π-complex are directly related to the Gibbs energy barrier difference between the Markonikov and anti-Markovnikov additions. It can be concluded that the coordination mode of the initial π-complex ultimately controls the regioselectivity ...
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.
