Ruthenium-catalyzed synthesis of highly substituted pyrroles from 1-vinylpropargyl alcohols and amines

Article abstract of DOI:10.1002/ejoc.201300803

Ruthenium-catalyzed atom-economic transformations of 1-vinylpropargyl alcohols with amines leading to highly substituted pyrroles in a one-pot cascade process are reported. The allylation/cycloisomerization sequence is catalyzed by a single ruthenium(0) complex that contains a redox-coupled dienone ligand and can be extended by an additional [3,3] rearrangement. The environmentally benign reactions allow the metal-catalyzed conversion of inexpensive and readily accessible materials to highly functionalized pyrroles with water as the only waste product. Ruthenium-catalyzed atom-economic transformations of 1-vinylpropargyl alcohols with primary amines leading to highly substituted pyrroles in a one-pot cascade process are reported. The allylation/ cycloisomerization cascade reaction generates water as the only waste product and the sequence can be extended by an additional [3,3] rearrangement by using secondary allylamines. Copyright