Improved arene fluorination methodology for I(III) salts.
نویسندگان
چکیده
The use of low polarity aromatic solvents (benzene or toluene) and/or the removal of inorganic salts results in dramatically improved yields of fluorinated arenes from diaryliodonium salts. This methodology is shown to "scale down" to the conditions used typically for radiotracer synthesis.
منابع مشابه
Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts.
For the first time it is shown that exceptionally electron-rich arene rings can be fluorinated exclusively during the reductive elimination reactions of diaryliodonium fluorides. The 5-methoxy[2.2]paracyclophan-4-yl directing group simultaneously reduces unproductive aryne chemistry and eliminates ligand exchange reactions by a combination of steric and electronic effects. Use of the cyclophane...
متن کاملSterically Congested 2,6‐Disubstituted Anilines from Direct C−N Bond Formation at an Iodine(III) Center
2,6-Disubstituted anilines are readily prepared from the direct reaction between amides and diaryliodonium salts. As demonstrated for 24 different examples, the reaction is of unusually broad scope with respect to the sterically congested arene and the nitrogen source, occurs without the requirement for any additional promoter, and proceeds through a direct reductive elimination at the iodine(I...
متن کاملSpecific reactivity of SH versus OH functions towards dinuclear arene ruthenium units: synthesis of cationic complexes of the type [(arene)2Ru2(SR)3]
The reaction of [(arene)RuCl2]2 (arene /C6H6, p -Me /C6H4 / i Pr, C6Me6) with p -thiocresol, 2-mercaptoethanol and p mercaptophenol in refluxing ethanol gives the tris-thiolato complexes [(arene)2Ru2(SR)3] (R /p -C6H4 /Me, CH2CH2OH, p C6H4OH) which can be isolated as the chloride salts. The remarkable selectivity of (arene)ruthenium units for SH versus OH functions reflects the affinity of ruth...
متن کاملCopper-Catalyzed [18F]Fluorination of (Mesityl)(aryl)iodonium Salts
A practical, rapid, and highly regioselective Cu-catalyzed radiofluorination of (mesityl)(aryl)iodonium salts is described. This protocol utilizes [(18)F]KF to access (18)F-labeled electron-rich, -neutral, and -deficient aryl fluorides under a single set of mild conditions. This methodology is applied to the synthesis of protected versions of two important radiotracers: 4-[(18)F]fluorophenylala...
متن کاملIodine(III) Reagents in Radical Chemistry
The chemistry of hypervalent iodine(III) compounds has gained great interest over the past 30 years. Hypervalent iodine(III) compounds show valuable ionic reactivity due to their high electrophilicity but also express radical reactivity as single electron oxidants for carbon and heteroatom radical generation. Looking at ionic chemistry, these iodine(III) reagents can act as electrophiles to eff...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic letters
دوره 12 15 شماره
صفحات -
تاریخ انتشار 2010