Pyrrole Synthesis Catalyzed by AgOTf or Cationic Au(I) Complexes
- 6 May 2006
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (12) , 4525-4529
- https://doi.org/10.1021/jo060382c
Abstract
Either silver trifluoromethanesulfonate or a mixture of gold(I) chloride, silver trifluoromethanesulfonate, and triphenylphosphine catalyze the formation of pyrroles from substituted β-alkynyl ketones and amines. The reactions proceed by using 5 mol % of catalyst with yields of isolated pyrroles ranging from 13% to 92%. Sixteen examples are used to compare the effectiveness of each catalyst.Keywords
This publication has 14 references indexed in Scilit:
- Direct Mannich and Nitro‐Mannich Reactions with Non‐Activated Imines: AgOTf‐Catalyzed Addition of Pronucleophiles to ortho‐Alkynylaryl Aldimines Leading to 1,2‐DihydroisoquinolinesAngewandte Chemie International Edition in English, 2005
- Gold(I)-Catalyzed Synthesis of Highly Substituted FuransOrganic Letters, 2005
- A Novel Class of in Vivo Active Anticancer Agents: Achiralseco-Amino- andseco-Hydroxycyclopropylbenz[e]indolone (seco-CBI) Analogues of the Duocarmycins and CC-1065Journal of Medicinal Chemistry, 2005
- Pt(II) or Ag(I) Salt Catalyzed Cycloisomerizations and Tandem Cycloadditions Forming Functionalized Azacyclic ArraysOrganic Letters, 2004
- Gold(I)‐Catalyzed 5‐endo‐dig Carbocyclization of Acetylenic Dicarbonyl CompoundsAngewandte Chemie International Edition in English, 2004
- Catalaytic Isomerization of 1,5-Enynes to Bicyclo[3.1.0]hexenesJournal of the American Chemical Society, 2004
- Isolation of Mangiferin fromBombax malabaricumand Structure Revision of ShamiminPlanta Medica, 2003
- Four New Bioactive Pyrrole-Derived Alkaloids from the Marine Sponge Axinella brevistylaJournal of Natural Products, 2001
- A new family of tricyclic alkaloids from Myrmicaria antsTetrahedron, 1996
- Funebradiol, a New Pyrrole Lactone Alkaloid from Quararibea funebris FlowersJournal of Natural Products, 1990