Direct C–H iodination of 1,3-azoles catalysed by CuBr 2

Nickel-catalyzed C−H arylation of benzoxazoles and oxazoles: Benchmarking the influence of electronic, steric and leaving group variations in phenolic electrophiles

“…16 Phenyl oxazole substrates 8 – 10 were prepared using literature procedures. 17 The pivalates, tosylates, mesylates and carbamates were prepared using literature procedures. 18 2-Fluoro-4-methoxy benzaldehyde, and 2-fluoro-5-methyl benzaldehyde were obtained from Matrix Scientific and used as received.…”

Recent Advances in First‐Row Transition‐Metal‐Mediated C−H Halogenation of (Hetero)arenes and Alkanes

“…In the same year, a methodology for direct CÀ H iodination of 1,3-azoles in the presence of Cu(II) salt, iodine, 1,10-phenanthroline, and a weaker base LiOt-Bu via subsequent metalation/iodination process was developed by Yu and co-workers. [206] Notably, several copper catalyzed/mediated strategies for the halogenation of 8-aminoquinolines have been reported by various research groups [207][208][209][210][211][212][213][214] since the initial report by Stahl and co-workers [204] for CÀ H chlorination of N-(8quinolinyl)benzamide (Scheme 69). In 2015, Xie and co-workers reported the regioselective C-5 chlorination of 8-acylaminoquinolines using stoichiometric amount of CuCl 2 as the halogenating source as well as the catalyst along with Cu(OAc) 2 as the base (i, Scheme 69).…”

A Simple and Efficient Iodination of Aromatic Compounds Using I2/Choline Chloride/K2S2O8

“…Plausible mechanism: We have proposed a plausible mechanism for iodination of aromatic compounds by molecular iodine and choline chloride/potassium peroxodisulfate; by homolytic cleavage under the influence of heat, in situ formed choline peroxodisulfate readily forms choline sulphate radical [1], which can be easily converted into choline sulphate anion [4] by one electron transfer from molecular iodine [3], so that molecular iodine is oxidized to iodonium cation radical [4]. The nucleophilic attack of iodonium cation radical on aromatic substrate produces an intermediate [6], which rapidly oxidized to iodinated aromatic compounds. The rate of the reaction may further accelerated by in situ formed HI acid (Scheme-III).…”

“…Many oxidizing agents have been considered for formation of I + like species either in situ or as stable isolable intermediates. Some examples of iodinating agents are: I2/CuBr2 [6], CsI3 [7], KF/I2 [8], I2/ HIO3/grinding [9], I2/Bi(NO3)3•5H2O-BiCl3 [10], I2/TMOF [11], NIS/In(OTf)3 [12], I2/silver nitrate [13], NIS/CF3CO2H [14], N-iodosaccharin [15], hydroxyl radicals/nanocrystalline CeO2/I2 [16], N-chlorosuccinimide and sodium iodide [17]. Recent methods for iodination of aromatic compounds includes the reactions catalyzed by NIS/Pd(OAc)2 [18] [19], I 2 /LiOtBu/1,10-phenanthroline [6], NIS/Ball milling [20], I 2 /Pd(OAc) 2 /CsOAc/NaHCO 3 [21].…”