The development of methods for the transition metal-catalysed functionalization of C-H bonds is revolutionizing synthetic organic chemistry by providing tools to simplify and accelerate the synthesis and modification of a myriad of known and still unknown organic molecules including aromatic compounds. However, in these processes, the ability to discriminate between C-H bonds for subsequent transformation into other functional groups still remains as a major challenge. To date, much progress has been made on developing strategies for the ortho-functionalization of arenes, mainly through the derivatization of the substrates with directing groups. meta-Functionalization approaches, on the other hand, are extremely scarce despite eta-substitution is a widespread motive amongst biologically active molecules.
The research outlined in this proposal aims at developing a process that makes use of CO2 as an invisible directing group leading to an array of novel direct meta-functionalization methodologies. To do so, we envision a one-pot strategy involving a carboxylation ortho to an R group followed by a tandem CO2H directed ortho-functionalization/decarboxylation process that affords the desired meta-functionalized products and releases again the CO2 employed as the directing group.
The realisation of the objectives of this project will push forward the state-of-the art in the area of C-H bond activation by providing step economical access to molecules that are difficult to prepare via conventional multistep routes.
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