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Mild and Rapid Aniline/HBF4 center dot DEE-Catalysed Formation of Sulfinyl Imines
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.ORCID iD: 0000-0001-6782-6622
2019 (English)In: ChemistrySelect, ISSN 2365-6549, Vol. 4, no 25, p. 7431-7436Article in journal (Refereed) Published
Abstract [en]

The combination of anline and tetrafluoroboric acid diethyl etherate (2.5 mol% and 5 mol%, respectively) significantly accelerates the formation of sulfinyl imines in dichloromethane and isopropylacetate at room temperature compared to previous procedures. A DFT and NMR spectroscopic study shows that the anilinium tetrafluoroborate complex is solvated by sulfinamide molecules in the initial state and that the rate-limiting step of the reaction is the addition of the sulfinamide molecule to the protonated aniline-based imine. In addition, the catalytic system was also utilised in a one-pot, two step reaction, where the in situ formed sulfinyl imine was arylated in a rhodium catalysed reaction with high diastereoselectivity.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2019. Vol. 4, no 25, p. 7431-7436
Keywords [en]
Sulfinylimines, Organic synthesis, Organocatalysis, DFT, NMR
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-255378DOI: 10.1002/slct.201901218ISI: 000474296800005Scopus ID: 2-s2.0-85068481356OAI: oai:DiVA.org:kth-255378DiVA, id: diva2:1339595
Note

QC 20190730

Available from: 2019-07-30 Created: 2019-07-30 Last updated: 2019-07-30Bibliographically approved

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Dinér, Peter

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