Abstract
Nitrogen heterocycles are found in a majority of approved small-molecule pharmaceuticals, and the number of approved fluorinated drugs is increasing each decade. Therefore, new approaches for accessing fluorinated nitrogen heterocycles are of great significance. A novel, scalable, and metal-free method for accessing a wide range of fluorinated indoles is described. This oxidative-dearomatization-enabled approach assembles 2-trifluoromethyl NH-indole products from simple commercially available anilines with hexafluoroacetylacetone in the presence of an organic oxidant. The nature of the aniline N-capping group is critical for the success of this new reaction. Furthermore, the indole products contain a 3-trifluoroacetyl group, which can be exploited to access a plethora of useful functional groups.
Original language | English (US) |
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Pages (from-to) | 2243-2247 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 55 |
Issue number | 6 |
DOIs | |
State | Published - Feb 5 2016 |
Externally published | Yes |
Keywords
- Dearomatization
- fluorine
- indoles
- nitrogen heterocycle
- synthetic methods
ASJC Scopus subject areas
- Catalysis
- General Chemistry
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CCDC 1434645: Experimental Crystal Structure Determination
Vitaku, E. (Creator), Smith, D. T. (Creator) & Njardarson, J. T. (Creator), Cambridge Crystallographic Data Centre, 2016
DOI: 10.5517/cc1k4vwf, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1k4vwf&sid=DataCite
Dataset
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CCDC 1434646: Experimental Crystal Structure Determination
Vitaku, E. (Creator), Smith, D. T. (Creator) & Njardarson, J. T. (Creator), Cambridge Crystallographic Data Centre, 2016
DOI: 10.5517/cc1k4vxg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1k4vxg&sid=DataCite
Dataset
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CCDC 1434647: Experimental Crystal Structure Determination
Vitaku, E. (Creator), Smith, D. T. (Creator) & Njardarson, J. T. (Creator), Cambridge Crystallographic Data Centre, 2016
DOI: 10.5517/cc1k4vyh, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1k4vyh&sid=DataCite
Dataset