Selective C–H bond functionalization of arenes continues to be an important avenue of research as a method to efficiently synthesize biologically relevant, substituted arenes from simple precursors. Conversion of unreactive C–H bonds to synthetically useful C–B bonds allows for production of value-added fine chemicals based on the versatility of the C–B bond in synthesis. The recently developed phosphine-directed C–H borylation provides a diverse group of ambiphilic phosphine boronates that can be used as bifunctional ligands, organocatalysts, and precursors to a range of functionalized phosphines. The discovery of an unusual cationic iridium pre-catalyst was found to expand the substrate scope significantly, providing selective mono-borylation, polyborylation, and benzylic borylation for select substrates. The nature of the accessible phosphine boronates will be discussed along with efforts to access enantioenriched phosphine boronates. Reactions that utilize the resulting phosphine boronate esters to access functionalized phosphines will also be addressed.

Accessing ambiphilic phosphine boronates by phosphine-directed C–H borylation

2019 Fall National Meeting

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