Biomaterial Database

Palladium-catalyzed 2-arylation of pyrroles. 2009

Daniel T Gryko, and Olena Vakuliuk, and Dorota Gryko, and Beata Koszarna

Institute of Organic Chemistry of the Polish Academy of Sciences, Warsaw, Poland. daniel@icho.edu.pl

A methodology that affords N-alkyl-2-arylpyrroles and N-aryl-2-arylpyrroles via direct coupling from aryl iodides has been developed. After examining various reaction parameters: solvent, ratio of reagents, catalyst, base and additives the optimal conditions for the condensation were identified. Two crucial factors, (a) anhydrous DMSO as solvent and (b) 5 M excess of pyrrole counterpart, were found to strongly influence the reaction outcome. The conditions identified (PdCl(2)(PPh(3))(2), AgOAc, anhyd DMSO, KF, 100 degrees C, 5 h) resulted in the formation of 2-arylpyrroles in 14-80% yield. Furthermore, the synthesis is compatible with electron-withdrawing and electron-donating groups on the aryl moiety.

UI	MeSH Term	Description	Entries
D008956	Models, Chemical	Theoretical representations that simulate the behavior or activity of chemical processes or phenomena; includes the use of mathematical equations, computers, and other electronic equipment.	Chemical Models,Chemical Model,Model, Chemical
D009942	Organometallic Compounds	A class of compounds of the type R-M, where a C atom is joined directly to any other element except H, C, N, O, F, Cl, Br, I, or At. (Grant & Hackh's Chemical Dictionary, 5th ed)	Metallo-Organic Compound,Metallo-Organic Compounds,Metalloorganic Compound,Organometallic Compound,Metalloorganic Compounds,Compound, Metallo-Organic,Compound, Metalloorganic,Compound, Organometallic,Compounds, Metallo-Organic,Compounds, Metalloorganic,Compounds, Organometallic,Metallo Organic Compound,Metallo Organic Compounds
D010165	Palladium	A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.
D011758	Pyrroles	Azoles of one NITROGEN and two double bonds that have aromatic chemical properties.	Pyrrole
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D004121	Dimethyl Sulfoxide	A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.	DMSO,Dimethyl Sulphoxide,Dimethylsulfoxide,Dimethylsulphinyl,Dimethylsulphoxide,Dimexide,Rheumabene,Rimso,Rimso 100,Rimso-50,Sclerosol,Sulfinylbis(methane),Rimso 50,Rimso50,Sulfoxide, Dimethyl,Sulphoxide, Dimethyl
D006844	Hydrocarbons, Cyclic	Organic compounds composed exclusively of carbon and hydrogen forming a closed ring that may be either alicyclic or aromatic.	Cyclic Hydrocarbons,Hydrocarbons, Polycyclic,Polycyclic Hydrocarbons
D006847	Hydrocarbons, Iodinated	Hydrocarbon compounds with one or more HYDROGEN atoms substituted with IODINE.	Iodinated Hydrocarbons
D012834	Silver	An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.
D012997	Solvents	Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant & Hackh's Chemical Dictionary, 5th ed)	Solvent