Iron(III) complexes of amine-bis(phenolate) ligands as catalysts for the C-C cross-coupling of aryl grignard reagents with benzyl halides

Chard, E. (2012) Iron(III) complexes of amine-bis(phenolate) ligands as catalysts for the C-C cross-coupling of aryl grignard reagents with benzyl halides. Masters thesis, Memorial University of Newfoundland.

[English] PDF - Accepted Version Available under License - The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission. Download (9MB)

Abstract

Traditionally, complexes containing heavy and precious metals such as palladium have been used to catalyze a wide range of C-C cross-coupling reactions. However, there are many drawbacks to using these types of catalysts because of their toxicity and/or price. More recently, in the interest of sustainability, there has been a rapid increase in the study of iron-based catalysts. Iron is inexpensive, non-toxic, environmentally benign, and readily available as it is one of the most abundant elements on Earth. -- The catalytic formation of diarylmethane motifs is a very important synthetic tool, with applications in pharmaceuticals and biologically active compounds. To date, the formation of diarylmethane motifs by the iron-catalyzed C-C cross-coupling of benzyl halides with aryl Grignard reagents has been reported to be unsatisfactory, giving low yields and poor electivity resulting in the formation of homocoupled by-products. The development of an air stable, non-hygroscopic, single component iron-based catalyst which can effectively generate diarylmethane motifs is of particular interest. -- Recent research in the Kozak group has focused on the use of iron(III) complexes supported by amine-bis(phenolate) ligands as potential catalysts for C-C cross-coupling reactions. A series of structurally authenticated iron(III) complexes of tridentate amine-bis(phenolate) ligands have been prepared and their potential as catalysts for the C-C cross-coupling of aryl Grignards with benzyl halides, including chlorides, has been explored. The results of catalysis studies, as well as structural and spectroscopic characterization of the metal complexes will be presented.

Actions (login required)

View Item