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Efficient Pathway for the Preparation of Aryl(isoquinoline)iodonium(III) Salts and Synthesis of Radiofluorinated Isoquinolines
Author(s) -
Yuan Zheliang,
Cheng Ran,
Chen Pinhong,
Liu Guosheng,
Liang Steven H.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201606381
Subject(s) - isoquinoline , mesoionic , chemistry , aryl , salt (chemistry) , carbene , yield (engineering) , halide , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , materials science , alkyl , metallurgy
Iodonium compounds play a pivotal role in 18 F‐fluorination of radiopharmaceuticals containing non‐activated arenes. However, preparation of these species is limited to oxidation conditions or exchange with organometallics that are prepared from aryl halides. Herein we describe a novel “one‐pot” process to assemble aryl(isoquinoline)iodonium salts in 40–94 % yields from mesoionic carbene silver complex and Aryl‐I‐Py 2 (OTf) 2 . The method is general, practical, and compatible with well‐functionalized molecules as well as useful for the preparation of a wide range of 18 F‐labeled isoquinolines resulting in up to 92 % radiochemical conversion. As proof of concept, a fluorinated isoquinoline alkaloid, 18 F‐aspergillitine is prepared in 10 % isolated radiochemical yield from the corresponding phenyl(aspergillitine)iodonium salt.