445399-49-5Relevant articles and documents
C-phosphorylation of N-arylpyrroles
Ivonin, Sergey P.,Tolmachev, Andrew A.,Pinchuk, Alexander M.
, p. 223 - 228 (2007/10/03)
Phosphorylation of N-arylpyrroles with phosphorus tribromide proceeds regioselectively at the position 2 of the heterocyclic system. A 2-to-3 migration of the dibromophosphino group has been discovered, with its ease depending on the electronic nature of a substituent on the phenyl ring, solvent polarity, and the presence of pyridine hydrobromide in the reaction mixture. Further phosphorylation of 2- and 3-monophosphorylated N-arylpyrroles regioselectively involves the respective positions 4 and 5 of the heterocycle and is governed by the electron-acceptor effect of the phosphorus-containing substituent.
