Introduction of an Effective and Economical Heterogeneous Ruthenium Catalyst for Regioselective Ring-Opening of Epoxides and the Friedel– Crafts Alkylation Reaction of Indoles and Pyrroles

Author(s): Khalil Tabatabaeian*, Mohammad Ali Zanjanchi, Nosrat. O. Mahmoodi, Tooraj Eftekhari.

Journal Name: Letters in Organic Chemistry

Volume 14 , Issue 3 , 2017

Become EABM
Become Reviewer

Graphical Abstract:


Abstract:

Background: Metal organic frameworks square measure crystalline materials with fascinating chemical and physical attributes that include metal ions or clusters and multidentate organic particles. MOFs acquire the expected traits to be employed in classical applications similar to heterogeneous catalysis and storage and separation of gases and different Compounds. Post-synthetic modification (PSM) is an associate replacement method to prepare functionalized MOFs.

Methods: The IRMOF-3-PI-RuCl3 was prepared by refluxing a combination of IRMOF-3-PI, [H(DMSO)2][RuCl4(DMSO)2] and ethanol. The amount of ruthenium metal in catalyst was found to be 2.35 w% based on ICP analysis. To perform the ring opening reaction, a solution of styrene oxide, indole, pyrole or alcohol nucleophile, in methanol, IRMOF-3-PI-RuCl3 was added. After completion of the reaction, the catalyst was precipitated.

Results: A MOF-supported metal catalyst (IRMOF-3-PI-RuCl3) was designed and synthesized by postsynthetic method. The BET surface area of the final catalyst was slightly reduced as determined by N2 sorption experiments. The results showed that the provided catalyst has a high potential for the ring opening of epoxides with alcohols, indoles and pyrroles under gentle conditions.

Conclusion: In summary, a simple, rapid, economical and an effective route for the alcoholysis of epoxides and therefore the Friedel-Crafts alkylation of indoles and pyrroles via an basically regioselective ring opening of epoxides with aliphatic and aromatic amines using IRMOF-3-PI-RuCl3 with cage type poriferous structure as heterogeneous catalysts, has been established. This methodology is very regioselective in numerous instances that give the products with high yield for e.g. in aromatic and aliphatic amines. Ease of separation and straightforward workup are among other advantages of this catalyst.

Keywords: Epoxides, heterogeneous catalysis, metal organic frameworks, nucleophiles, ring-opening, ruthenium.

Rights & PermissionsPrintExport Cite as


Article Details

VOLUME: 14
ISSUE: 3
Year: 2017
Page: [207 - 217]
Pages: 11
DOI: 10.2174/1570178614666170117152437
Price: $58

Article Metrics

PDF: 17
HTML: 2