Open AccessNucleophilic (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 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 , fluoride , potassium fluoride , potassium , combinatorial chemistry , organic chemistry , inorganic 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.