Publication

Chemoselective Hydrogenation and Transfer Hydrogenation of Aldehydes Catalyzed by Iron(II) PONOP Pincer Complexes

Rosario Scopelliti, Xile Hu, Simona Mazza
2015
Journal Articles

Abstract

Iron-catalyzed hydrogenation has drawn much attention, yet the scope and chemoselectivity of iron catalysis warrant further improvement. Here we report new iron pincer complexes as chemoselective hydrogenation and transfer hydrogenation catalysts. Several Fe(II) complexes supported by a 2,6-bis(phosphinito)pyridine ligand (PONOP) have been synthesized. Fe(II) hydride complexes [((PrPONOP)-Pr-i)Fe(CO)(H)Br] (2) and ((PrPONOP)-Pr-i)Fe(CO)(H)(CH3CN) (3) can activate H-2 at room temperature. Complexes 2 and 3 are hydrogenation catalysts at room temperature, and the hydrogenation is selective for aldehyde in the presence of ketone and alkene groups. 2 and 3 are also chemoselective transfer hydrogenation catalysts using sodium formate as the hydride source.

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https://infoscience.epfl.ch/entities/publication/4d69df3c-47e4-434b-829a-bb87602a0ac0

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Rosario Scopelliti, Xile Hu, Simona Mazza
2015
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/4d69df3c-47e4-434b-829a-bb87602a0ac0

About this result

Related concepts (27)

Asymmetric hydrogenation

Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional spatial selectivity. Critically, this selectivity does not come from the target molecule itself, but from other reagents or catalysts present in the reaction. This allows spatial information (what chemists refer to as chirality) to transfer from one molecule to the target, forming the product as a single enantiomer.

Transfer hydrogenation

In chemistry, transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular . It is applied in laboratory and industrial organic synthesis to saturate organic compounds and reduce ketones to alcohols, and imines to amines. It avoids the need for high-pressure molecular used in conventional hydrogenation. Transfer hydrogenation usually occurs at mild temperature and pressure conditions using organic or organometallic catalysts, many of which are chiral, allowing efficient asymmetric synthesis.

Hydrogenation

Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures.

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