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

66 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

Access to Document

10.1021/jacs.6b06770

Cite this

@article{e08802e5148f4180b843e423217bdd6d,

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.\}",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = aug,

day = "31",

doi = "10.1021/jacs.6b06770",

language = "English (US)",

volume = "138",

pages = "10802--10805",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "34",

}

TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/84984856780

UR - https://www.scopus.com/inward/citedby.url?scp=84984856780&partnerID=8YFLogxK

U2 - 10.1021/jacs.6b06770

DO - 10.1021/jacs.6b06770

M3 - Article

C2 - 27500313

AN - SCOPUS:84984856780

SN - 0002-7863

VL - 138

SP - 10802

EP - 10805

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 34

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this