New Transition Metal Catalysed Methods for Alkyl C-N Bond Formation

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Forming bonds between carbon and nitrogen (C-N bonds) is an important process in organic chemistry but in many instances this represents a very difficult task. The goal of this research proposal is to provide new methods, which involve metal catalysts, for particularly challenging types of C-N bond formation: Part 1. The first area will look at is forming C-N bonds in an intramolecular fashion. We will investigate cases where the carbon atom is bonded to three other atoms, of which at least one is another carbon atom. Here, we will develop a method which forms this type of C-N bond from a simple alkene precursor. In this area we will also look at the possibility of controlling which mirror image of the C-N bond we form. This particular aspect is of relevance in cases where the carbon atom of the C-N bond is attached to three other different groups.Part 2. The second area we will look at is forming C-N bonds in an intermolecular manner. These processes will be much more challenging to develop and we will use the knowledge we gain from Part 1 to aid this aspect.To facilitate these new methods we will examine the chemistry of a specific nitrogenous organic functionality that allows redox neutral C-N bond forming processes; this, in combination with a metal catalyst, will act as the source of nitrogen. The new C-N bond forming reactions will initially be developed in systems where this functionality is part of the same molecule as the alkene with which it reacts. When the new C-N bond forms a ring structure will therefore be generated. As our understanding of the reactions improves, we will see if the organic functionality and alkene can be part of different molecules. This type of C-N bond formation is anticipated to be much more challenging. This research area has been chosen because C-N bonds are vital components in living structures (e.g. amino acids) and drug compounds. By developing these new reactions we will be providing methods which allow chemists to make biologically important molecules in a quicker and more efficient manner. Indeed, these new reactions may even allow people to make molecules which are presently inaccessible. In the long term, this research can benefit wider society by enabling the development of drugs for the treatment of illnesses or by providing molecular probes for understanding biological processes. Additionally, there is an inherent need for new C-N bond forming processes as many current methods are subject to patent protection (e.g. the Buchwald-Hartwig amination) which can limit their deployment in industrial settings.Aspects of this research programme have previously been submitted as part of a successful EPSRC CAF application which was not taken up by the PI as a Royal Society URF was accepted instead.