Iridium-Catalyzed Enantioselective C-H Borylation of Diarylphosphinates

P-stereogenic phosphorus compounds are a ubiquitous and critically important class of chiral ligands in asymmetric catalysis. Methods for catalytic asymmetric synthesis via a step- and atom-economic way are still very limited. We herein disclose a protocol of phosphinate-directed iridium-catalyzed enantioselective ortho-H borylation to construct P-stereogenic phosphorus compounds. A number of functional groups could be well tolerated to afford optically active diarylphosphinates with good to excellent enantioselectivities (up to 92% ee). We also demonstrate the synthetic utilities of the obtained borylated products, including the synthesis of precursors for chiral phosphine ligands.

Automated summary

This study presents a novel method for the synthesis of P-stereogenic phosphorus compounds through phosphinate-directed iridium-catalyzed reactions, with high yields and good enantioselectivities. The borylated products synthesized can be used for the preparation of precursors for chiral phosphine ligands, showing potential industrial applications.