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C-H Borylation Catalysts that Distinguish Between Similarly Sized Substituents Like Fluorine and Hydrogen. | LitMetric

AI Article Synopsis

  • Modifying the steric and electronic profiles of ligands allows for selective C-H borylation in aromatic compounds, especially in regions with subtle steric differences.
  • The research highlights significant variations in reaction selectivities between two borane reagents, Bpin and HBpin, for the first time.
  • Using carefully chosen ligand and borane combinations enables highly regioselective C-H borylation in cases where standard methods yield low selectivity.

Article Abstract

By modifying ligand steric and electronic profiles it is possible to C-H borylate ortho or meta to substituents in aromatic and heteroaromatic compounds, where steric differences between accessible C-H sites are small. Dramatic effects on selectivities between reactions using Bpin or 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin) are described for the first time. Judicious ligand and borane combinations give highly regioselective C-H borylations on substrates where typical borylation protocols afford poor selectivities.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9864527PMC
http://dx.doi.org/10.1021/acs.orglett.9b02299DOI Listing

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