Nuclear fluorination of 3,5-diarylisoxazoles with Selectfluor®

Chad E. Stephens; Jacqueline A. Blake

doi:10.1016/j.jfluchem.2004.08.001

Nuclear fluorination of 3,5-diarylisoxazoles with Selectfluor®

Chad E. Stephens, Jacqueline A. Blake

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

23 Scopus citations

Abstract

C-4 Fluorination of a series of 3,5-diarylisoxazoles has been accomplished using the N-F reagent Selectfluor ^®. With substrates containing neutral or activating substituents on the 5-phenyl ring, acetonitrile at room temperature or at reflux could be used as solvent. However, when deactivating substituents were present, a higher reaction temperature was required for which sulfolane was found to be a good solvent. At this higher temperature, a unique trifluorination of the isoxazole nucleus by an addition mechanism occurred as a side reaction.

Original language	English (US)
Pages (from-to)	1939-1945
Number of pages	7
Journal	Journal of Fluorine Chemistry
Volume	125
Issue number	12
DOIs	https://doi.org/10.1016/j.jfluchem.2004.08.001
State	Published - Dec 2004
Externally published	Yes

Keywords

Fluorination
Heterocycle
Isoxazole
Selectfluor
Substituent effects
Sulfolane

ASJC Scopus subject areas

Biochemistry
Environmental Chemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.jfluchem.2004.08.001

Cite this

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title = "Nuclear fluorination of 3,5-diarylisoxazoles with Selectfluor{\textregistered}",

abstract = "C-4 Fluorination of a series of 3,5-diarylisoxazoles has been accomplished using the N-F reagent Selectfluor {\textregistered}. With substrates containing neutral or activating substituents on the 5-phenyl ring, acetonitrile at room temperature or at reflux could be used as solvent. However, when deactivating substituents were present, a higher reaction temperature was required for which sulfolane was found to be a good solvent. At this higher temperature, a unique trifluorination of the isoxazole nucleus by an addition mechanism occurred as a side reaction.",

keywords = "Fluorination, Heterocycle, Isoxazole, Selectfluor, Substituent effects, Sulfolane",

author = "Stephens, {Chad E.} and Blake, {Jacqueline A.}",

note = "Funding Information: We thank the Georgia State University Research Fund and the Georgia Research Alliance for financial support. We also thank Air Products and Chemicals Inc., for the generous gift of Selectfluor {\textregistered} and Dr. Markus Germann for assistance in obtaining the high-field 13 C NMR of compound 6d . ",

year = "2004",

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doi = "10.1016/j.jfluchem.2004.08.001",

language = "English (US)",

volume = "125",

pages = "1939--1945",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier BV",

number = "12",

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TY - JOUR

T1 - Nuclear fluorination of 3,5-diarylisoxazoles with Selectfluor®

AU - Stephens, Chad E.

AU - Blake, Jacqueline A.

N1 - Funding Information: We thank the Georgia State University Research Fund and the Georgia Research Alliance for financial support. We also thank Air Products and Chemicals Inc., for the generous gift of Selectfluor ® and Dr. Markus Germann for assistance in obtaining the high-field 13 C NMR of compound 6d .

PY - 2004/12

Y1 - 2004/12

N2 - C-4 Fluorination of a series of 3,5-diarylisoxazoles has been accomplished using the N-F reagent Selectfluor ®. With substrates containing neutral or activating substituents on the 5-phenyl ring, acetonitrile at room temperature or at reflux could be used as solvent. However, when deactivating substituents were present, a higher reaction temperature was required for which sulfolane was found to be a good solvent. At this higher temperature, a unique trifluorination of the isoxazole nucleus by an addition mechanism occurred as a side reaction.

AB - C-4 Fluorination of a series of 3,5-diarylisoxazoles has been accomplished using the N-F reagent Selectfluor ®. With substrates containing neutral or activating substituents on the 5-phenyl ring, acetonitrile at room temperature or at reflux could be used as solvent. However, when deactivating substituents were present, a higher reaction temperature was required for which sulfolane was found to be a good solvent. At this higher temperature, a unique trifluorination of the isoxazole nucleus by an addition mechanism occurred as a side reaction.

KW - Fluorination

KW - Heterocycle

KW - Isoxazole

KW - Selectfluor

KW - Substituent effects

KW - Sulfolane

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DO - 10.1016/j.jfluchem.2004.08.001

M3 - Article

AN - SCOPUS:11444261929

SN - 0022-1139

VL - 125

SP - 1939

EP - 1945

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

IS - 12

ER -

Nuclear fluorination of 3,5-diarylisoxazoles with Selectfluor®

Abstract

Keywords

ASJC Scopus subject areas

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