- Unexpected Behavior of the Heaviest Halogen Astatine in the Nucleophilic Substitution of Aryliodonium Salts
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Aryliodonium salts have become precursors of choice for the synthesis of18F-labeled tracers for nuclear imaging. However, little is known on the reactivity of these compounds with heavy halides, that is, radioiodide and astatide, at the radiotracer scale. In the first comparative study of radiohalogenation of aryliodonium salts with125I?and211At?, initial experiments on a model compound highlight the higher reactivity of astatide compared to iodide, which could not be anticipated from the trends previously observed within the halogen series. Kinetic studies indicate a significant difference in activation energy (Ea=23.5 and 17.1 kcal mol?1with125I?and211At?, respectively). Quantum chemical calculations suggest that astatination occurs via the monomeric form of an iodonium complex whereas iodination occurs via a heterodimeric iodonium intermediate. The good to excellent regioselectivity of halogenation and high yields achieved with diversely substituted aryliodonium salts indicate that this class of compounds is a promising alternative to the stannane chemistry currently used for heavy radiohalogen labeling of tracers in nuclear medicine.
- Guérard, Fran?ois,Lee, Yong-Sok,Baidoo, Kwamena,Gestin, Jean-Fran?ois,Brechbiel, Martin W.
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supporting information
p. 12332 - 12339
(2016/08/24)
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- CuBr catalyzed C-N cross coupling reaction of purines and diaryliodonium salts to 9-arylpurines
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CuBr was found to be an efficient catalyst for the C-N cross coupling reaction of purine and diaryliodonium salts. 9-Arylpurines were synthesized in excellent yields with short reaction times (2.5 h). The method represents an alternative to the synthesis of 9-arylpurines via Cu(ii) catalyzed C-N coupling reaction with arylboronic acids as arylating agents. The Royal Society of Chemistry 2011.
- Niu, Hong-Ying,Xia, Chao,Qu, Gui-Rong,Zhang, Qian,Jiang, Yi,Mao, Run-Ze,Li, De-Yang,Guo, Hai-Ming
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supporting information; experimental part
p. 5039 - 5042
(2011/08/07)
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