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|Title:||A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions|
|Title:||Chemistry - a European journal|
|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|
|Date of registration:||10-Sep-2019|
|Faculty:||NT - Naturwissenschaftlich- Technische Fakultät|
|Department:||NT - Chemie|
|Professorship:||NT - Arbeitsgruppe für Organische Chemie|
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