Please use this identifier to cite or link to this item: doi:10.22028/D291-28766
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Title: Nucleophilic Substitutions of Alcohols in High Levels of Catalytic Efficiency
Author(s): Stach, Tanja
Dräger, Julia
Huy, Peter
Language: English
Title: Organic letters
Volume: 20
Issue: 10
Startpage: 2980
Endpage: 2983
Publisher/Platform: American Chemical Society (ACS)
Year of Publication: 2018
Publikation type: Journal Article
Abstract: A practical method for the nucleophilic substitution (S N) of alcohols furnishing alkyl chlorides, bromides, and iodides under stereochemical inversion in high catalytic efficacy is introduced. The fusion of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent allows notable turnover numbers up to 100. Moreover, the use of plain acetyl chloride as a stoichiometric promotor in an invertive S N-type transformation is demonstrated for the first time. The operationally straightforward protocol exhibits high levels of stereoselectivity and scalability and tolerates a variety of functional groups.
DOI of the first publication: 10.1021/acs.orglett.8b01023
URL of the first publication: https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.8b01023?rand=v3v0k487
Link to this record: hdl:20.500.11880/27726
http://dx.doi.org/10.22028/D291-28766
ISSN: 1523-7060
1523-7052
Date of registration: 10-Sep-2019
Faculty: NT - Naturwissenschaftlich- Technische Fakultät
Department: NT - Chemie
Professorship: NT - Arbeitsgruppe für Organische Chemie
Collections:UniBib – Die Universitätsbibliographie

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