40073-12-9Relevant academic research and scientific papers
Carbonyl-Olefin Metathesis Catalyzed by Molecular Iodine
Tran, Uyen P. N.,Oss, Giulia,Breugst, Martin,Detmar, Eric,Pace, Domenic P.,Liyanto, Kevin,Nguyen, Thanh V.
, p. 912 - 919 (2019/01/14)
The carbonyl-olefin metathesis reaction could facilitate rapid functional group interconversion and allow construction of complicated organic structures. Herein, we demonstrate that elemental iodine, a very simple catalyst, can efficiently promote this chemical transformation under mild reaction conditions. Our mechanistic studies revealed intriguing aspects of the activation mode via molecular iodine and the iodonium ion that could change the previously established perception of catalyst and substrate design for the carbonyl-olefin metathesis reaction.
Tropylium-promoted carbonyl-olefin metathesis reactions
Tran, Uyen P.N.,Oss, Giulia,Pace, Domenic P.,Ho, Junming,Nguyen, Thanh V.
, p. 5145 - 5151 (2018/06/21)
The carbonyl-olefin metathesis (COM) reaction is a highly valuable chemical transformation in a broad range of applications. However, its scope is much less explored compared to analogous olefin-olefin metathesis reactions. Herein we demonstrate the use of tropylium ion as a new effective organic Lewis acid catalyst for both intramolecular and intermolecular COM and new ring-opening metathesis reactions. This represents a significant improvement in substrate scope from recently reported developments in this field.
Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis
McAtee, Christopher C.,Riehl, Paul S.,Schindler, Corinna S.
supporting information, p. 2960 - 2963 (2017/03/11)
Polycyclic aromatic hydrocarbons are important structural motifs in organic chemistry, pharmaceutical chemistry, and materials science. The development of a new synthetic strategy toward these compounds is described based on the design principle of iron(III)-catalyzed carbonyl-olefin metathesis reactions. This approach is characterized by its operational simplicity, high functional group compatibility, and regioselectivity while relying on FeCl3 as an environmentally benign, earth-abundant metal catalyst. Experimental evidence for oxetanes as reactive intermediates in the catalytic carbonyl-olefin ring-closing metathesis has been obtained.
