Developing Catalytic Enantioselective Fluorination
The background that led to the development ofthe first catalytic and enantioselective carbon-fluorine bond-forming reaction is presented. Two different approaches, i.e. the use of nucleophilic and electrophilic fluorinating agents, respectively, have been pursued. Well-defined RU(II) 16-el...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
2001-10-01
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| Series: | CHIMIA |
| Subjects: | |
| Online Access: | https://chimia.ch/chimia/article/view/3488 |
| _version_ | 1818281911419666432 |
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| author | Antonio Togni Antonio Mezzetti Peter Barthazy Claus Becker Ingrid Devillers Richard Frantz Lukas Hintermann Mauro Perseghini Maria Sanna |
| author_facet | Antonio Togni Antonio Mezzetti Peter Barthazy Claus Becker Ingrid Devillers Richard Frantz Lukas Hintermann Mauro Perseghini Maria Sanna |
| author_sort | Antonio Togni |
| collection | DOAJ |
| description |
The background that led to the development ofthe first catalytic and enantioselective carbon-fluorine bond-forming reaction is presented. Two different approaches, i.e. the use of nucleophilic and electrophilic fluorinating agents, respectively, have been pursued. Well-defined
RU(II) 16-electron systems of the type [RuF(PP)2]+ (where PP is a chelating diphosphine), as well as analogous complexes containing tetradentate PNNP ligands, were found to catalyze the halogen exchange reaction of activated alkyl chlorides, bromides, and iodides in the
presence of TIF as the fluorine source. Isolable crystalline [TiCI2 (TADDOLato)] complexes are efficient catalysts in the enantioselective fluorination of 2-substituted 1,3-dicarbonyl compounds with Selectfluor® (also called F-TEDA; 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane
bis{tetrafluoroborate}). Levels of enantioselectivity up to 90% ee were obtained.
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| first_indexed | 2024-12-13T00:12:38Z |
| format | Article |
| id | doaj.art-1e204b200ded4f87896ccaab020a620d |
| institution | Directory Open Access Journal |
| issn | 0009-4293 2673-2424 |
| language | deu |
| last_indexed | 2024-12-13T00:12:38Z |
| publishDate | 2001-10-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj.art-1e204b200ded4f87896ccaab020a620d2022-12-22T00:05:53ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24242001-10-015510Developing Catalytic Enantioselective FluorinationAntonio TogniAntonio MezzettiPeter BarthazyClaus BeckerIngrid DevillersRichard FrantzLukas HintermannMauro PerseghiniMaria Sanna The background that led to the development ofthe first catalytic and enantioselective carbon-fluorine bond-forming reaction is presented. Two different approaches, i.e. the use of nucleophilic and electrophilic fluorinating agents, respectively, have been pursued. Well-defined RU(II) 16-electron systems of the type [RuF(PP)2]+ (where PP is a chelating diphosphine), as well as analogous complexes containing tetradentate PNNP ligands, were found to catalyze the halogen exchange reaction of activated alkyl chlorides, bromides, and iodides in the presence of TIF as the fluorine source. Isolable crystalline [TiCI2 (TADDOLato)] complexes are efficient catalysts in the enantioselective fluorination of 2-substituted 1,3-dicarbonyl compounds with Selectfluor® (also called F-TEDA; 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis{tetrafluoroborate}). Levels of enantioselectivity up to 90% ee were obtained. https://chimia.ch/chimia/article/view/3488Asymmetric catalysisEnantioselective chlorinationEnantioselective fluorinationRuthenium fluoro complexesTitanium taddolato complexes |
| spellingShingle | Antonio Togni Antonio Mezzetti Peter Barthazy Claus Becker Ingrid Devillers Richard Frantz Lukas Hintermann Mauro Perseghini Maria Sanna Developing Catalytic Enantioselective Fluorination CHIMIA Asymmetric catalysis Enantioselective chlorination Enantioselective fluorination Ruthenium fluoro complexes Titanium taddolato complexes |
| title | Developing Catalytic Enantioselective Fluorination |
| title_full | Developing Catalytic Enantioselective Fluorination |
| title_fullStr | Developing Catalytic Enantioselective Fluorination |
| title_full_unstemmed | Developing Catalytic Enantioselective Fluorination |
| title_short | Developing Catalytic Enantioselective Fluorination |
| title_sort | developing catalytic enantioselective fluorination |
| topic | Asymmetric catalysis Enantioselective chlorination Enantioselective fluorination Ruthenium fluoro complexes Titanium taddolato complexes |
| url | https://chimia.ch/chimia/article/view/3488 |
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