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Synfacts 2025; 21(01): 75
DOI: 10.1055/a-2467-4870
Organo- and Biocatalysis

Brønsted Acid–HFIP Combination Allows Amination of 2-Arylethanols via Phenonium Intermediate

Contributor(s):
Benjamin List 
,
Layth Alama 
Van Hoof M, Mayer RJ, Moran J, Leboeuf D *. Universite de Strasbourg, France
Triflic Acid-Catalyzed Dehydrative Amination of 2-Arylethanols with Weak N-Nucleophiles in Hexafluoroisopropanol.

Angew. Chem. Int. Ed. 2024;
DOI: 10.1002/anie.202417089
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Keywords

amination - HFIP - TfOH - phenonium

Significance

Leboeuf and coworkers report a Brønsted acid catalyzed methodology that enables the direct amination of 2-arylethanols eliminating the need of pre activation of the alcohol moiety. This transformation proceeds only in fluorinated solvents, namely HFIP giving access to a wide range of valuable products.


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Comment

Direct amination reactions are of high value to rapidly access nitrogen containing products. The authors present a simple protocol to introduce weak N-nucleophiles giving access to high value products in excellent yields (up to 95 %) while generating only water as a byproduct.


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Publication History

Article published online:
20 December 2024

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