A Comparative Study on the Utility of Metal Triflates as Catalysts for the Allyation of Aromatic Acetals and Dioxolanes

Brendan O'Donnell, Illinois Wesleyan University
Justin Feng, Illinois Wesleyan University
DoHun Lee, Faculty Advisor, Illinois Wesleyan University
Ram Mohan, Faculty Advisor, Illinois Wesleyan University

Description

Acetals are useful protecting groups in organic synthesis, but they can also be converted to other useful functional groups. For example, the synthesis of homoallyl ethers via allylation of acetals is an important synthetic transformation involving the formation of carbon-carbon bonds, and as such, has been the subject of several studies. However, most methodologies employed in the allylation of acetals require reagents that are either toxic, highly corrosive, or are used in stoichiometric amounts, such as TiCl4, AlCl3, TMSOTf, and trifluoroacetic acid. With increasing environmental concerns, it is imperative to develop new methods that utilize reagents that are both efficient and environmentally benign. Thus, our interest in expanding on the current methodologies used in the allylation of acetals prompted us to investigate the utility of hitherto underutilized metal triflate catalysts, iron(III) triflate and erbium(III) triflate. The results of this study will be presented.

 
Apr 12th, 2:00 PM Apr 12th, 3:00 PM

A Comparative Study on the Utility of Metal Triflates as Catalysts for the Allyation of Aromatic Acetals and Dioxolanes

Center for Natural Sciences, Illinois Wesleyan University

Acetals are useful protecting groups in organic synthesis, but they can also be converted to other useful functional groups. For example, the synthesis of homoallyl ethers via allylation of acetals is an important synthetic transformation involving the formation of carbon-carbon bonds, and as such, has been the subject of several studies. However, most methodologies employed in the allylation of acetals require reagents that are either toxic, highly corrosive, or are used in stoichiometric amounts, such as TiCl4, AlCl3, TMSOTf, and trifluoroacetic acid. With increasing environmental concerns, it is imperative to develop new methods that utilize reagents that are both efficient and environmentally benign. Thus, our interest in expanding on the current methodologies used in the allylation of acetals prompted us to investigate the utility of hitherto underutilized metal triflate catalysts, iron(III) triflate and erbium(III) triflate. The results of this study will be presented.