Silylimidazolium Hexafluorophosphate Salts as Synthetic Precursors to N‑Heterocyclic Carbene Pentafluorophosphorus Adducts

N-Heterocyclic carbene pentafluorophosphorus (NHC-PF5) adducts are six-coordinate phosphorus­(v) compounds with emerging applications but poor synthetic accessibility. We have developed a simple and high yielding protocol for synthesizing imidazolylidene NHC-PF5 adducts from silylimidazolium hexaflu...

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Bibliographic Details
Published inOrganic letters Vol. 26; no. 22; pp. 4750 - 4755
Main Authors Rowsey, Rylan A., Hilgar, Jeremy D., Romero, Nathan A.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.05.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Letter
Physical Sciences
Science & Technology
PHOSPHORUS(V) FLUORIDES
PERFLUORINATED COMPLEX ANIONS
ALKALI-METAL SALTS
IMIDAZOLIUM
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Summary:N-Heterocyclic carbene pentafluorophosphorus (NHC-PF5) adducts are six-coordinate phosphorus­(v) compounds with emerging applications but poor synthetic accessibility. We have developed a simple and high yielding protocol for synthesizing imidazolylidene NHC-PF5 adducts from silylimidazolium hexafluorophosphate salts. Using this methodology, we have prepared a series of NHC-PF5 adducts in high yields, including new NHC-PF5 building blocks amenable to subsequent synthetic diversification. We also demonstrate that a similar approach enables access to analogous, synthetically elusive NHC-BF3 and NHC-SbF5 adducts.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01549