NUK - logo
E-viri
Celotno besedilo
Recenzirano
  • Polypyridyl iridium(III) ba...
    Pandrala, Mallesh; Resendez, Angel; Malhotra, Sanjay V.

    Journal of catalysis, 10/2019, Letnik: 378
    Journal Article

    Highly efficient and chemoselective transfer hydrogenation of aldehydes has been achieved using polypyridyl iridium(III) catalysts in aqueous ethanol, with sodium formate as the hydride source. Successful reduction of acidic and hydroxy groups containing aldehydes can be achieved in basic and acidic reaction conditions, demonstrating the efficiency of the catalyst in a broad pH range with high conversion rates under microwave irradiation. Display omitted •Highly efficient polypyridyl iridium(III) based catalysts.•Effective at a broad pH range for chemoselective reduction.•Catalysts are air stable, easy to prepare.•Method is applicable for a wide range of substrates.•These catalysts are capable of reducing all 2-, 3- and 4-carboxy benzaldehydes at different pH. 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.