Palladium-Catalyzed Coupling Reactions on Functionalized 2-Trifluoromethyl-4-chromenone Scaffolds: Synthesis of Highly Functionalized Trifluoromethyl Heterocycles

Javier Izquierdo; Atul D. Jain; Sarki A. Abdulkadir; Gary E. Schiltz

doi:10.1055/s-0037-1610669

Synthesis, Table of Contents

Synthesis 2019; 51(06): 1342-1352
DOI: 10.1055/s-0037-1610669

paper

Palladium-Catalyzed Coupling Reactions on Functionalized 2-Trifluoromethyl-4-chromenone Scaffolds: Synthesis of Highly Functionalized Trifluoromethyl Heterocycles

Javier Izquierdo *

^aCenter for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, IL 60208, USA Email: javier.izquierdo-ferrer@northwestern.edu

,

Atul D. Jain

^aCenter for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, IL 60208, USA Email: javier.izquierdo-ferrer@northwestern.edu

,

Sarki A. Abdulkadir

^bDepartment of Urology, Northwestern University, Chicago, IL 60611, USA

^cRobert H. Lurie Comprehensive Cancer Center, Feinberg School of Medicine, Northwestern University, Chicago, IL 60611, USA

,

Gary E. Schiltz

^aCenter for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, IL 60208, USA Email: javier.izquierdo-ferrer@northwestern.edu

^cRobert H. Lurie Comprehensive Cancer Center, Feinberg School of Medicine, Northwestern University, Chicago, IL 60611, USA

^dDepartment of Pharmacology, Northwestern University, Chicago, IL 60611, USA

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Abstract

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Abstract

The chromenone core is an ubiquitous group in biologically active natural products and has been extensively used in organic synthesis. Fluorine-derived compounds, including those with a trifluoromethyl group (CF₃), have shown enhanced biological activities in numerous pharmaceuticals compared with their non-fluorinated analogues. 2-Trifluoromethylchromenones can be readily functionalized at the 8- and 7-positions, providing chromenones cores of high structural complexity, which are excellent precursors for numerous trifluoromethyl heterocycles.

Key words

fluorine - chromenone - trifluoromethyl heterocycle synthesis - palladium-catalyzed coupling

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References

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