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doi:10.22028/D291-28767
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: | https://onlinelibrary.wiley.com/doi/epdf/10.1002/chem.201800588 |
Link to this record: | hdl:20.500.11880/27728 http://dx.doi.org/10.22028/D291-28767 |
ISSN: | 0947-6539 1521-3765 |
Date of registration: | 10-Sep-2019 |
Faculty: | NT - Naturwissenschaftlich- Technische Fakultät |
Department: | NT - Chemie |
Professorship: | NT - Arbeitsgruppe für Organische Chemie |
Collections: | SciDok - Der Wissenschaftsserver der Universität des Saarlandes |
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