Selective defunctionalisation of organic molecules to valuable intermediates is a fundamentally important transformation in organic synthesis. Despite the advances made in efficient and selective defunctionalisation using transition-metal catalysis, the cost, toxicity, and non-renewable properties limit its application in industrial manufacturing processes. In this regard, boron Lewis acid catalysis has emerged as a powerful tool for the cleavage of carbon-heteroatom bonds. The ground-breaking finding is that the strong boron Lewis acid B(C6F5)3 can activate Si-H bonds through η1 coordination, and this Lewis adduct is a key intermediate that enables various reduction processes. This system can be tuned by variation of the electronic and structural properties of the borane catalyst, and together with different hydride sources high chemoselectivity can be achieved. This Perspective provides a comprehensive summary of various defunctionalisation reactions such as deoxygenation, decarbonylation, desulfurisation, deamination, and dehalogenation, all of which catalysed by boron Lewis acids. This journal is © The Royal Society of Chemistry.
Citation
Huaquan Fang, Martin Oestreich. Defunctionalisation catalysed by boron Lewis acids. Chemical science. 2020 Jul 28;11(47):12604-12615
PMID: 34094457
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