Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion

Erin E. Gray; Matthew K. Nielsen; Kimberly A. Choquette; Julia A. Kalow; Thomas J.A. Graham; Abigail G. Doyle

doi:10.1021/jacs.6b06770

Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion

Erin E. Gray, Matthew K. Nielsen, Kimberly A. Choquette, Julia A. Kalow, Thomas J.A. Graham, Abigail G. Doyle

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

60 Scopus citations

Abstract

The copper-catalyzed H-F insertion into α-diazocarbonyl compounds is described using potassium fluoride (KF) and hexafluoroisopropanol. Access to complex α-fluorocarbonyl derivatives is achieved under mild conditions, and the method is readily adapted to radiofluorination with [¹⁸F]KF. This late-stage strategy provides an attractive route to ¹⁸F-labeled biomolecules.

Original language	English (US)
Pages (from-to)	10802-10805
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	34
DOIs	https://doi.org/10.1021/jacs.6b06770
State	Published - Aug 31 2016

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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title = "Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion",

abstract = "The copper-catalyzed H-F insertion into α-diazocarbonyl compounds is described using potassium fluoride (KF) and hexafluoroisopropanol. Access to complex α-fluorocarbonyl derivatives is achieved under mild conditions, and the method is readily adapted to radiofluorination with [18F]KF. This late-stage strategy provides an attractive route to 18F-labeled biomolecules.",

author = "Gray, {Erin E.} and Nielsen, {Matthew K.} and Choquette, {Kimberly A.} and Kalow, {Julia A.} and Graham, {Thomas J.A.} and Doyle, {Abigail G.}",

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T1 - Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion

AU - Gray, Erin E.

AU - Nielsen, Matthew K.

AU - Choquette, Kimberly A.

AU - Kalow, Julia A.

AU - Graham, Thomas J.A.

AU - Doyle, Abigail G.

PY - 2016/8/31

Y1 - 2016/8/31

N2 - The copper-catalyzed H-F insertion into α-diazocarbonyl compounds is described using potassium fluoride (KF) and hexafluoroisopropanol. Access to complex α-fluorocarbonyl derivatives is achieved under mild conditions, and the method is readily adapted to radiofluorination with [18F]KF. This late-stage strategy provides an attractive route to 18F-labeled biomolecules.

AB - The copper-catalyzed H-F insertion into α-diazocarbonyl compounds is described using potassium fluoride (KF) and hexafluoroisopropanol. Access to complex α-fluorocarbonyl derivatives is achieved under mild conditions, and the method is readily adapted to radiofluorination with [18F]KF. This late-stage strategy provides an attractive route to 18F-labeled biomolecules.

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IS - 34

ER -

Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion

Abstract

All Science Journal Classification (ASJC) codes

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