Polypyridyl iridium(III) based catalysts for highly chemoselective hydrogenation of aldehydes

Mallesh Pandrala, Angel Resendez, Sanjay V. Malhotra

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Iridium-catalyzed transfer hydrogenation (TH) of carbonyl compounds using HCOOR (R = H, Na, NH4) as a hydrogen source is a pivotal process as it provides the clean process and is easy to execute. However, the existing highly efficient iridium catalysts work at a narrow pH; thus, does not apply to a wide variety of substrates. Therefore, the development of a new catalyst which works at a broad pH range is essential as it can gain a broader scope of utilization. Here we report highly efficient polypyridyl iridium(III) catalysts, [Ir(tpy)(L)Cl](PF6)2 {where tpy = 2,2′:6′,2′'-Terpyridine, L = phen (1,10-Phenanthroline), Me2phen (4,7-Dimethyl-1,10-phenanthroline), Me4phen (3,4,7,8-Tetramethyl-1,10-phenanthroline), Me2bpy (4,4′-Dimethyl-2–2′-dipyridyl)} for the chemoselective reduction of aldehydes to alcohols in aqueous ethanol and sodium formate as the hydride source. The reaction can be carried out efficiently in broad pH ranges, from pH 6 to 11. These catalysts are air stable, easy to prepare using commercially available starting materials, and are highly applicable for a wide range of substrates, such as electron-rich or deficient (hetero)arenes, halogens, phenols, alkoxy, ketones, esters, carboxylic acids, cyano, and nitro groups. Particularly, acid and hydroxy groups containing aldehydes were reduced successfully in basic and acidic reaction conditions, demonstrating the efficiency of the catalyst in a broad pH range with high conversion rates under microwave irradiation.

Original languageEnglish (US)
Pages (from-to)283-288
Number of pages6
JournalJournal of Catalysis
Volume378
DOIs
StatePublished - Oct 2019
Externally publishedYes

Keywords

  • Aldehydes
  • Chemoselectivity
  • Polypyridyl iridium(III) complexes
  • Transfer hydrogenation

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

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