Journal ArticleDOI
Fluorinated enol ethers: their synthesis and reactivity
TLDR
The present review lists different methods for the preparation of fluorinated enol ethers, and sums up their numerous synthetic applications.Abstract:
Thanks to the beneficial effect of fluorine substitution on the pharmacokinetic properties of molecules, an ever increasing number of marketed drugs incorporate a fluorine atom into their structure. As a consequence, the synthesis of fluorinated molecules has become a very active research field. Among the numerous approaches, fluorinated enol ethers are valuable building blocks that allow the introduction of a fluoro- or difluoromethyl group through a wide variety of reactions. The present review lists different methods for their preparation and sums up their numerous synthetic applications.read more
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Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles
TL;DR: The phosphoramide-based bifunctional catalysts achieved better enantiofacial control than the analogous H-bond-donor-derived catalysts in these reactions, suggesting the potential of the former in new chiral catalyst development.
Journal ArticleDOI
Recent advances in the synthesis and CF functionalization of gem-difluoroalkenes
Xuxue Zhang,Song Cao +1 more
TL;DR: In the past two decades, significant progress has been made to the development of efficient methods for the construction of gem-difluoroalkenes and useful reactions involving the cleavage of CF bond as mentioned in this paper.
Journal ArticleDOI
Experimental and Theoretical Studies on Rhodium-Catalyzed Coupling of Benzamides with 2,2-Difluorovinyl Tosylate: Diverse Synthesis of Fluorinated Heterocycles
Jia-Qiang Wu,Shang-Shi Zhang,Hui Gao,Zisong Qi,Chu-Jun Zhou,Wei-Wei Ji,Yao Liu,Yunyun Chen,Qingjiang Li,Xingwei Li,Honggen Wang +10 more
TL;DR: This work reports on the synthesis of four types of fluorinated heterocycles via rhodium(III)-catalyzed C-H activation of arenes/alkenes and versatile coupling with 2,2-difluorovinyl tosylate and the origins of the intriguing selectivity in the competing β-F elimination versus C-N bond formation were elucidated.
Journal ArticleDOI
Highly Stereoselective Gold-Catalyzed Coupling of Diazo Reagents and Fluorinated Enol Silyl Ethers to Tetrasubstituted Alkenes
TL;DR: A highly stereoselective synthesis of all-carbon or fluorinated tetrasubstituted alkenes from diazo reagents and fluorinated enol silyl ethers, using C-F bond as a synthetic handle is reported.
Journal ArticleDOI
Recent Advances in Transition Metal-Catalyzed Functionalization of gem-Difluoroalkenes.
Suvajit Koley,Ryan A. Altman +1 more
TL;DR: Recent (since 2017) transition metal-catalyzed transformations of these specialized alkenes are reviewed and general reactivity patterns of these reactions are summarized.
References
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Journal ArticleDOI
Fluorine in Pharmaceuticals: Looking Beyond Intuition.
TL;DR: Experimental progress in exploration of the specific influence of carbon-fluorine single bonds on docking interactions is reviewed and complementary analysis based on comprehensive searches in the Cambridge Structural Database and the Protein Data Bank is added.
Journal ArticleDOI
Understanding organofluorine chemistry. An introduction to the C–F bond
TL;DR: Fundamental aspects of the C-F bond are explored to rationalise the geometry, conformation and reactivity of individual organofluorine compounds.
Journal ArticleDOI
Introduction of Fluorine and Fluorine-Containing Functional Groups
TL;DR: This Review gives a brief summary of conventional fluorination reactions, including those reactions that introduce fluorinated functional groups, and focuses on modern developments in the field.
Journal ArticleDOI
C-F bond activation in organic synthesis.
Hideki Amii,Kenji Uneyama +1 more
TL;DR: Organic fluorine compounds have received a great deal of interest and attention from the scientists involved in diverse fields of science and technology and not only C-F bond formation but also selective C-f bond activation have become current subjects of active investigation from the viewpoint of effective synthesis of fluoroorganic compounds.
Journal ArticleDOI
A new method for aromatic difluoromethylation: copper-catalyzed cross-coupling and decarboxylation sequence from aryl iodides.
TL;DR: A new methodology for aromatic difluoromethylation is described and it is shown that Aryl iodides reacted with α-silyldifluoroacetates upon treatment with copper catalyst in DMSO or DME to give the corresponding aryldif LUacetates in moderate to good yields.