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Noda H, Bode JW. Synthesis of chemically and configurationally stable monofluoro acylboronates: effect of ligand structure on their formation, properties, and reactivities. J Am Chem Soc. 2015;137(11):3958-66doi: 10.1021/jacs.5b00822.
Noda, H., & Bode, J. W. (2015). Synthesis of chemically and configurationally stable monofluoro acylboronates: effect of ligand structure on their formation, properties, and reactivities. Journal of the American Chemical Society, 137(11), 3958-66. https://doi.org/10.1021/jacs.5b00822
Noda, Hidetoshi, and Bode, Jeffrey W. "Synthesis of chemically and configurationally stable monofluoro acylboronates: effect of ligand structure on their formation, properties, and reactivities." Journal of the American Chemical Society vol. 137,11 (2015): 3958-66. doi: https://doi.org/10.1021/jacs.5b00822
Noda H, Bode JW. Synthesis of chemically and configurationally stable monofluoro acylboronates: effect of ligand structure on their formation, properties, and reactivities. J Am Chem Soc. 2015 Mar 25;137(11):3958-66. doi: 10.1021/jacs.5b00822. Epub 2015 Mar 13. PMID: 25723308.
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J Am Chem Soc. 2015 Mar 25;137(11):3958-66. doi: 10.1021/jacs.5b00822. Epub 2015 Mar 13.

Synthesis of chemically and configurationally stable monofluoro acylboronates: effect of ligand structure on their formation, properties, and reactivities.

Journal of the American Chemical Society

Hidetoshi Noda, Jeffrey W Bode

Affiliations

  1. LaboratoriumfurOrganischeChemie, Department of Chemistry and Applied Biosciences, ETH-Zurich, 8093 Zurich, Switzerland.

PMID: 25723308 DOI: 10.1021/jacs.5b00822

Abstract

The recent disclosures of two classes of acylborons, potassium acyltrifluoroborates (KATs) and N-methyliminodiacetyl (MIDA) acylboronates, demonstrated that certain acylboron species can be both remarkably stable and uniquely reactive. Here we report new classes of ligands for acylboronates that have a significant influence on the formation, properties, and reactivities of acylboronates. Our systematic investigations identified a class of neutral, monofluoroboronates that can be prepared in a one step, gram-scale fashion from readily accessible KATs. These monofluoroboronates are stable to air, moisture, and silica gel chromatography and can be easily handled without any special precautions. X-ray crystallography, NMR spectroscopy, and HPLC studies showed that they are tetravalent, configurationally stable B-chiral acylboronates. Significantly, the ligands on the boronate allow for fine-tuning of the properties and reactivity of acylboronates. In amide-forming ligation with hydroxylamines under aqueous conditions, a considerable difference in reactivity was observed as a function of ligand structure. The solid-state structures suggested that subtle steric and conformational factors modulate the reactivities of the acylboronates.

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