1008533-34-3Relevant academic research and scientific papers
Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium-zinc base and regioselectivity-computed CH acidity relationship
Messaoud, Mohamed Yacine Ameur,Bentabed-Ababsa, Ghenia,Hedidi, Madani,Derdour, A?cha,Chevallier, Floris,Halauko, Yury S.,Ivashkevich, Oleg A.,Matulis, Vadim E.,Picot, Laurent,Thiéry, Valérie,Roisnel, Thierry,Dorcet, Vincent,Mongin, Florence
, p. 1475 - 1485 (2015)
The synthesis of N-arylated pyrroles and indoles is documented, as well as their functionalization by deprotonative metallation using the base in situ prepared from LiTMP and ZnCl2·TMEDA (1/3 equiv). With N-phenylpyrrole and -indole, the reactions were carried out in hexane containing TMEDA which regioselectively afforded the 2-iodo derivatives after subsequent iodolysis. With pyrroles and indoles bearing N-substituents such as 2-thienyl, 3-pyridyl, 4-methoxyphenyl and 4-bromophenyl, the reactions all took place on the substituent, at the position either adjacent to the heteroatom (S, N) or ortho to the heteroatom-containing substituent (OMe, Br). The CH acidities of the substrates were determined in THF solution using the DFT B3LYP method in order to rationalize the experimental results.
Ligand-activated lithium-mediated zincation of N-phenylpyrrole
Seggio, Anne,Lannou, Marie-Isabelle,Chevallier, Floris,Nobuto, Daisuke,Uchiyama, Masanobu,Golhen, Stephane,Roisnel, Thierry,Mongin, Florence
, p. 9982 - 9989 (2007)
Metalation of N-phenylpyrrole by using an in situ mixture of ZnCl 2·TMEDA (0.5 equiv; TMEDA = N,N,N′,N′- tetramethylethylenediamine) and LiTMP (1.5 equiv; TMP = 2,2,6,6- tetramethylpiperidino) was optimized. The reaction carried out at room tem
