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Ruthenium‐Catalyzed Synthesis of Highly Substituted Pyrroles from 1‐Vinylpropargyl Alcohols and Amines
Author(s) -
Thies Nora,
Gerlach Martin,
Haak Edgar
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300803
Subject(s) - ruthenium , chemistry , cycloisomerization , catalysis , ligand (biochemistry) , combinatorial chemistry , atom economy , organic chemistry , redox , alcohol oxidation , biochemistry , receptor
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.