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doi:10.22028/D291-28766
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: | SciDok - Der Wissenschaftsserver der Universität des Saarlandes |
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