Please use this identifier to cite or link to this item: doi:10.22028/D291-28767
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Title: A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions
Author(s): Filbrich, Isabel
Huy, Peter
Language: English
Title: Chemistry - a European journal
Volume: 24
Issue: 29
Startpage: 7410
Endpage: 7416
Publisher/Platform: Wiley
Year of Publication: 2018
Publikation type: Journal Article
Abstract: A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN 2 inversion, which demonstrates the high practical value of the presented method.
DOI of the first publication: 10.1002/chem.201800588
URL of the first publication:
Link to this record: hdl:20.500.11880/27728
ISSN: 0947-6539
Date of registration: 10-Sep-2019
Faculty: NT - Naturwissenschaftlich- Technische Fakultät
Department: NT - Chemie
Professorship: NT - Arbeitsgruppe für Organische Chemie
Collections:Die Universitätsbibliographie

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