Multigram synthesis ofN-alkylbis-ureas for asymmetric hydrogen bonding phase-transfer catalysis

Anna Chiara Vicini, Gabriele Pupo, Francesco Ibba, Véronique Gouverneur

Published: 2021-11-09 DOI: 10.1038/s41596-021-00625-y

asymmetric hydrogen bonding

phase-transfer catalysis

N-alkylbis-ureas

enantioselective nucleophilic fluorinations

organocatalysts

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Fluorine is a key element present in ~35% of agrochemicals and 25% of marketed pharmaceutical drugs. The availability of reliable synthetic protocols to prepare catalysts that allow the efficient incorporation of fluorine in organic molecules is t
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ACKNOWLEDGMENTS

Pihko, P. M., ed. Hydrogen Bonding in Organic Synthesis (Wiley-VCH, 2009).
Taylor, M. S. & Jacobsen, E. N. Asymmetric catalysis by chiral hydrogen-bond donors. Angew. Chem. Int. Ed. Engl. 45, 1520–1543 (2006).
Doyle, A. G. & Jacobsen, E. N. Small-molecule H-bond donors in asymmetric catalysis. Chem. Rev. 107, 5713–5743 (2007).
Brak, K. & Jacobsen, E. N. Asymmetric ion-pairing catalysis. Angew. Chem. Int. Ed. Engl. 52, 534–561 (2013).
Ford, D. D., Lehnherr, D., Kennedy, C. R. & Jacobsen, E. N. Anion-abstraction catalysis: the cooperative mechanism of α-chloroether activation by dual hydrogen-bond donors. ACS Catal. 6, 4616–4620 (2016).
Pfeifer, L. et al. Hydrogen-bonded homolopetic fluoride-diarylurea complexes: structure, reactivity and coordinating power. J. Am. Chem. Soc. 138, 13314–13325 (2016).
Zhou, Y., Zhang, J. F. & Yoon, J. Fluorescence and colorimetric chemosensors for fluoride-ion detection. Chem. Rev. 114, 5511–5571 (2014).
Pupo, G. et al. Asymmetric nucleophilic fluorination under hydrogen bonding phase-transfer catalysis. Science 360, 368–642 (2018).
Pupo, G. et al. Hydrogen bonding phase-transfer catalysis with potassium fluoride: enantioselective synthesis of β-fluoroamines. J. Am. Chem. Soc. 141, 2878–2883 (2019).
Roagna, G. et al. Hydrogen bonding phase-transfer catalysis with ionic reactants: enantioselective synthesis of γ-fluoroamines. J. Am. Chem. Soc. 142, 14045–14051 (2020).
Harsanyi, A. & Sandford, G. Organofluorine chemistry: applications, sources and sustainability. Green. Chem. 17, 2081–2086 (2015).
Ibba, F. et al. Impact of multiple hydrogen bonds with fluoride on catalysis: insight from NMR spectroscopy. J. Am. Chem. Soc. 142, 19731–19744 (2020).
Kim, K. H., Lee, D.-W., Lee, Y.-S., Ko, D.-H. & Ha, D.-C. Enantioselective oxidative coupling of methyl-3-hydroxy-2-naphthoate using mono-N-alkylatedoctahydrobinaphthyl-2,20-diamine ligand. Tetrahedron 60, 9037–9042 (2004).
Cotarca, L., Geller, T. & Répási, J. Bis(trichloromethyl)carbonate (BTC, triphosgene): a safer alternative to phosgene? Org. Process Res. Dev. 21, 1439–1446 (2017).

关键词

asymmetric hydrogen bonding

phase-transfer catalysis

N-alkylbis-ureas

enantioselective nucleophilic fluorinations

organocatalysts

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