Diiminium Nucleophile Adducts Are Stable and Convenient Strong Lewis Acids
Bormann, N., Ward, J. S., Bergmann, A. K., Wenz, P., Rissanen, K., Gong, Y., Hatz, W., Burbaum, A., & Mulks, F. F. (2023). Diiminium Nucleophile Adducts Are Stable and Convenient Strong Lewis Acids. Chemistry : A European Journal, 29(58), Article e202302089. https://doi.org/10.1002/chem.202302089
Julkaistu sarjassa
Chemistry : A European JournalTekijät
Päivämäärä
2023Tekijänoikeudet
© 2023 the Authors
Strong Lewis acids are essential tools for manifold chemical procedures, but their scalable deployment is limited by their costs and safety concerns. We report a scalable, convenient, and inexpensive synthesis of stable diiminium-based reagents with a Lewis acidic carbon centre. Coordination with pyridine donors stabilises these centres; the 2,2’-bipyridine adduct shows a chelation effect at carbon. Due to high fluoride, hydride, and oxide affinities, the diiminium pyridine adducts are promising soft and hard Lewis acids. They effectively produce acylpyridinium salts from carboxylates that can acylate amines to give amides and imides even from electronically intractable coupling partners.
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WileyISSN Hae Julkaisufoorumista
0947-6539Asiasanat
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https://converis.jyu.fi/converis/portal/detail/Publication/184686941
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Lisätietoja rahoituksesta
This work was supported by the Fonds der Chemischen Industrie through a Liebig Fellowship (Li 210/01, F.F.M.) and by the Alexander von Humboldt Foundation through a Feodor Lynen Return Fellowship (F.F.M.) and through a Humboldt Research Award (K.R.). Generous support was received through materials and infrastructure by Carsten Bolm, his group, and the Institute for Organic Chemistry at the RWTH Aachen University. Computing resources were granted by the RWTH Aachen University under project rwth0928. Open Access funding enabled and organized by Projekt DEAL. ...Lisenssi
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