Heterocarboxylation is an organometallic transformation that yields highly versatile carboxylic acid derivatives. The increased synthetic value stems from the installation of a functionalizable carbon-boron bond that can be used as a building block in organic synthesis. Our lab reported the first methodology to achieve the boracarboxylation of vinyl arenes using a copper catalyst system. We have gained access to a new class of boron-based NSAID derivatives, containing the phenyl propionic acid pharmacophore, which may have some therapeutic potential. The heteroatom functionality provides access to useful products through subsequent synthetic elaboration. One specific reaction of interest is transforming the boracarboxylic acid into a novel borafluorolactonate “Molander” salt, which will allow for cross-coupling at the C-B bond.<br/>

Expansion of boracarboxylated vinyl arenes: Exploring the synthetic elaboration of the carbon-boron bond through cross-coupling

254th National Meeting (2017)

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