title: Sustainable Pathways to Pyrroles through Iron-Catalyzed N-Heterocyclization from Unsaturated Diols and Primary Amines.
abstract: Pyrroles are prominent scaffolds in pharmaceutically active compounds and play an important role in medicinal chemistry. Therefore, the development of new, atom-economic, and sustainable catalytic strategies to obtain these moieties is highly desired. Direct catalytic pathways that utilize readily available alcohol substrates have been recently established; however, these approaches rely on the use of noble metals such as ruthenium or iridium. Here, we report on the direct synthesis of pyrroles using a catalyst based on the earth-abundant and inexpensive iron. The method uses 2-butyne-1,4-diol or 2-butene-1,4-diol that can be directly coupled with anilines, benzyl amines, and aliphatic amines to obtain a variety of N-substituted pyrroles in moderate-to-excellent isolated yields.
authors: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, Netherlands.
authors: Tao
authors: T
authors: Yan
authors: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, Netherlands. k.barta@rug.nl.
authors: Katalin
authors: K
authors: Barta
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006018:Glycols / Q000737:chemistry*; D007501:Iron / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D000588:Amines; D006018:Glycols; D011758:Pyrroles; D007501:Iron
keywords: amines; dehydrogenation; diols; iron catalysis; pyrrole synthesis