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

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

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

Author(s) -

Erin E. Gray,

Matthew K. Nielsen,

Kimberly A. Choquette,

Julia A. Kalow,

Thomas J. A. Graham,

Abigail G. Doyle

Publication year - 2016

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.6b06770

Subject(s) - chemistry , copper , nucleophile , catalysis , medicinal chemistry , combinatorial chemistry , organic chemistry

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 [(18)F]KF. This late-stage strategy provides an attractive route to (18)F-labeled biomolecules.

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