Palladium Catalyzed, Multicomponent Synthesis of Fused-Ring Pyrroles from Aryl Iodides, Carbon Monoxide, and Alkyne-Tethered Imines.
J Org Chem. 2016 11 18; 81(22):11145-11152.JO

Abstract

A palladium-catalyzed multicomponent route to polycyclic pyrroles is described. Pd(PtBu3)2 was found to catalyze the coupling of (hetero)aryl iodides, two equivalents of carbon monoxide and alkyne-tethered imines into 1,3-dipoles (Münchnones), which undergo spontaneous, intramolecular 1,3-dipolar cycloaddition to form polycyclic pyrroles. The systematic variation of the alkyne, tethered-imine, or aryl iodide can allow the buildup of a range of pyrrole derivatives, where any of the substituents can be independently varied. In addition, the same palladium catalyst can be employed in an initial Sonogashira-type coupling with aryl iodides, which upon the addition of CO can allow the novel tandem catalytic, five component synthesis of diversely substituted products.

Authors+Show Affiliations

Firoozi N

Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada. Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad , Mashhad 9177948974, Iran.

Torres GM

Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.

Arndtsen BA

Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

27726363

Citation

Firoozi, Neda, et al. "Palladium Catalyzed, Multicomponent Synthesis of Fused-Ring Pyrroles From Aryl Iodides, Carbon Monoxide, and Alkyne-Tethered Imines." The Journal of Organic Chemistry, vol. 81, no. 22, 2016, pp. 11145-11152.

Firoozi N, Torres GM, Arndtsen BA. Palladium Catalyzed, Multicomponent Synthesis of Fused-Ring Pyrroles from Aryl Iodides, Carbon Monoxide, and Alkyne-Tethered Imines. J Org Chem. 2016;81(22):11145-11152.

Firoozi, N., Torres, G. M., & Arndtsen, B. A. (2016). Palladium Catalyzed, Multicomponent Synthesis of Fused-Ring Pyrroles from Aryl Iodides, Carbon Monoxide, and Alkyne-Tethered Imines. The Journal of Organic Chemistry, 81(22), 11145-11152.

Firoozi N, Torres GM, Arndtsen BA. Palladium Catalyzed, Multicomponent Synthesis of Fused-Ring Pyrroles From Aryl Iodides, Carbon Monoxide, and Alkyne-Tethered Imines. J Org Chem. 2016 11 18;81(22):11145-11152. PubMed PMID: 27726363.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Palladium Catalyzed, Multicomponent Synthesis of Fused-Ring Pyrroles from Aryl Iodides, Carbon Monoxide, and Alkyne-Tethered Imines. AU - Firoozi,Neda, AU - Torres,Gerardo M, AU - Arndtsen,Bruce A, Y1 - 2016/10/19/ PY - 2016/10/12/pubmed PY - 2016/10/12/medline PY - 2016/10/12/entrez SP - 11145 EP - 11152 JF - The Journal of organic chemistry JO - J Org Chem VL - 81 IS - 22 N2 - A palladium-catalyzed multicomponent route to polycyclic pyrroles is described. Pd(PtBu3)2 was found to catalyze the coupling of (hetero)aryl iodides, two equivalents of carbon monoxide and alkyne-tethered imines into 1,3-dipoles (Münchnones), which undergo spontaneous, intramolecular 1,3-dipolar cycloaddition to form polycyclic pyrroles. The systematic variation of the alkyne, tethered-imine, or aryl iodide can allow the buildup of a range of pyrrole derivatives, where any of the substituents can be independently varied. In addition, the same palladium catalyst can be employed in an initial Sonogashira-type coupling with aryl iodides, which upon the addition of CO can allow the novel tandem catalytic, five component synthesis of diversely substituted products. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/27726363/Palladium_Catalyzed_Multicomponent_Synthesis_of_Fused_Ring_Pyrroles_from_Aryl_Iodides_Carbon_Monoxide_and_Alkyne_Tethered_Imines_ DB - PRIME DP - Unbound Medicine ER -

Tags

Palladium Catalyzed, Multicomponent Synthesis of Fused-Ring Pyrroles from Aryl Iodides, Carbon Monoxide, and Alkyne-Tethered Imines.J Org Chem. 2016 11 18; 81(22):11145-11152.JO