Metal-free, one-pot conversion of proline derivatives into 2-aryl-3-iodo pyrrolidines by a sequential scission–iodination–arylation process

Abstract

The metal-free, direct conversion of readily available proline derivatives into 2-aryl-3-iodopyrrolidines is carried out under mild conditions and in good yields, using a sequential radical decarboxylation–oxidation–iodination–arylation reaction. These iodinated pyrrolidines are valuable precursors of other compounds. For instance, they can be cyclized to tricyclic compounds or undergo dehalogenation to 2-aryl-2,5-dihydro-1H-pyrroles, which are iminosugar and 2-arylpyrrole precursors. This process provides a short pathway to a variety of alkaloid and drug analogues of potential pharmaceutical interest.