Alkynes as Masked Ylides. A Concept for New Reactions and Reactivity

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Ylides are very useful reagents with a diverse range of reactivity, employed in the synthesis of small and large, simple and complex molecules. However, as ylides are sensitive species they can be introduced into a molecule only immediately prior to their use. Their synthetic precursors are also highly reactive species which cannot be carried through other manipulations.So whilst the ylide reactions themselves can be very effective, the long, inefficient, inflexible and intolerant strategies required to introduce them into a molecule, reduces their potential applicability. Similarly, the economy and efficiency of any synthesis that employs them is adversely affected.In this proposed research, a novel catalytic process will allow ylides to be prepared in situ, from robust functionality which can be carried through a variety of transformations unscathed. The flexible strategy to access a range of different ylides, coupled with their subsequent reactions will lead to a diverse array of new transformations. This new approach will result in more economical synthesis by utilising the power of ylide chemistry, whilst bypassing lengthy and inefficent starting material preparations. The resulting synthetic strategies will be shorter and more efficient than at present, with less chemical and time resource consumed and less waste produced.