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

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

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

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 (CF ₃ ), 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.

Original language	English (US)
Pages (from-to)	1342-1352
Number of pages	11
Journal	Synthesis (Germany)
Volume	51
Issue number	6
DOIs	https://doi.org/10.1055/s-0037-1610669
State	Published - 2019

Keywords

chromenone
fluorine
palladium-catalyzed coupling
trifluoromethyl heterocycle synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0037-1610669

Cite this

@article{88b825ed10f4485795d70cc128530449,

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

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 (CF 3 ), 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. ",

keywords = "chromenone, fluorine, palladium-catalyzed coupling, trifluoromethyl heterocycle synthesis",

author = "Javier Izquierdo and Jain, {Atul D.} and Abdulkadir, {Sarki A.} and Schiltz, {Gary E.}",

note = "Funding Information: This work was performed in the Northwestern University Medicinal and Synthetic Chemistry Core (ChemCore) at the Center for Molecular Innovation and Drug Discovery (CMIDD), which received funding from the Chicago Biomedical Consortium with support from The Searle Funds at The Chicago Community Trust. Financial support from Cancer Center Support Grant P30 CA060553 from the National Cancer Institute awarded to the Robert H. Lurie Comprehensive Cancer Center is also gratefully acknowledged. Funding from the National Cancer Institute of the National Institutes of Health under Award Number R01CA189074 is also acknowledged.NationalCancerInstituteoftheNationalInstitutesofHealth(P30CA060553)NationalCancerInstituteoftheNationalInstitutesofHealth(R01CA189074) Publisher Copyright: {\textcopyright} 2019 Georg Thieme Verlag. All rights reserved.",

year = "2019",

doi = "10.1055/s-0037-1610669",

language = "English (US)",

volume = "51",

pages = "1342--1352",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "6",

}

TY - JOUR

T1 - Palladium-Catalyzed Coupling Reactions on Functionalized 2-Trifluoromethyl-4-chromenone Scaffolds

T2 - Synthesis of Highly Functionalized Trifluoromethyl Heterocycles

AU - Izquierdo, Javier

AU - Jain, Atul D.

AU - Abdulkadir, Sarki A.

AU - Schiltz, Gary E.

N1 - Funding Information: This work was performed in the Northwestern University Medicinal and Synthetic Chemistry Core (ChemCore) at the Center for Molecular Innovation and Drug Discovery (CMIDD), which received funding from the Chicago Biomedical Consortium with support from The Searle Funds at The Chicago Community Trust. Financial support from Cancer Center Support Grant P30 CA060553 from the National Cancer Institute awarded to the Robert H. Lurie Comprehensive Cancer Center is also gratefully acknowledged. Funding from the National Cancer Institute of the National Institutes of Health under Award Number R01CA189074 is also acknowledged.NationalCancerInstituteoftheNationalInstitutesofHealth(P30CA060553)NationalCancerInstituteoftheNationalInstitutesofHealth(R01CA189074) Publisher Copyright: © 2019 Georg Thieme Verlag. All rights reserved.

PY - 2019

Y1 - 2019

N2 - 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 (CF 3 ), 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.

AB - 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 (CF 3 ), 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.

KW - chromenone

KW - fluorine

KW - palladium-catalyzed coupling

KW - trifluoromethyl heterocycle synthesis

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U2 - 10.1055/s-0037-1610669

DO - 10.1055/s-0037-1610669

M3 - Article

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AN - SCOPUS:85062342455

SN - 0039-7881

VL - 51

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EP - 1352

JO - Synthesis

JF - Synthesis

IS - 6

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 1840656: Experimental Crystal Structure Determination

CCDC 1840657: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1840656: Experimental Crystal Structure Determination

CCDC 1840657: Experimental Crystal Structure Determination

Cite this