Development of N,O Chelated Complexes for the Catalytic Synthesis of Amines and Nitrogen Containing Materials

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Amine functionalities are incorporated into a broad range of natural products called alkaloids and are key components of a majority of synthetic and naturally occurring biologically active chemicals and materials, such as pharmaceuticals, agrochemicals and anti-microbial plastics. Methods for selectively and strategically synthesizing such amine functionalized small molecules and materials from more readily available starting materials, including alkenes and alcohols, is an area of intense investigation with catalytic approaches emerging as the preferred strategy for improving energy efficiency and reducing waste by-product formation. Catalysts offer cutting-edge opportunities for advancing manufacturing efficiency and commercial profitability as they help chemical transformations occur with less forcing conditions and they control the outcome of the chemical reaction while not being consumed themselves. Thus, catalysts can be reused repeatedly and are only required in small amounts. This proposal targets the preparation of new catalysts for the efficient synthesis of value-added selectively substituted amines from inexpensive amine, alkene and alcohol starting materials. Such transformations have been targeted by the chemical/pharmaceutical/agrochemical manufacturing sector for decades, but are known to be challenging as the amine reagents and products can bind to catalysts and render them ineffective. Our group has pioneered the development of bio-inspired, N,O-chelated metal complexes as a new family of catalysts that are capable of assembling more complex amines from simple amine, alkene and alcohol building blocks by either catalytic C-N bond formation or C-C bond formation. Here we propose to build upon our previous successes to tackle known challenging transformations that at present have no generally effective catalytic option. Additionally, we propose to develop improved catalysts to build amines that cannot be readily assembled using traditional chemical approaches. Our core discoveries focus on realizing and understanding new chemical reactivity and transformations, which could be used to achieve innovative and cutting-edge approaches in chemical manufacturing. Benefits to Canada will include the development of world-leading clean technologies for the preparation of amine functionalized small molecules and materials of relevance to the plastics, composite materials, agrochemical and pharmaceutical industries.