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Bis(tri‐ tert ‐butylphosphine)palladium(0)‐Catalyzed Iodine–Fluorine Exchange at closo ‐Carboranes
Author(s) -
Ishita Keisuke,
Khalil Ahmed,
Tiwari Rohit,
Gallucci Judith,
Tjarks Werner
Publication year - 2018
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201800486
Subject(s) - chemistry , halogen , nucleophile , fluorine , palladium , carborane , catalysis , halogenation , fluoride , iodine , fluorocarbon , medicinal chemistry , organic chemistry , inorganic chemistry , alkyl
The bis(tri‐ tert ‐butylphosphine)palladium(0) [Pd( t Bu 3 P) 2 ]‐catalyzed synthesis of fluorinated closo ‐carboranes from 3D aromatic iodo‐ closo ‐carboranes by nucleophilic halogen exchange using silver(I) fluoride is described. Fluorination of 2‐iodo‐ closo ‐ p ‐carborane proceeded more readily than that of 9‐iodo‐ closo ‐ m ‐carborane. Iodine–fluorine exchange at 9‐iodo‐ closo ‐ o ‐carborane was not successful yielding instead a charge‐compensated dibutylphosphonio nido ‐ o ‐carborane. The described methodology advances the understanding of nucleophilic fluorination at aromatic systems by Pd 0 /Pd II catalysis. With further optimization, it could find application in the synthesis of 18 F‐labeled carboranyl diagnostics for biomedical applications.