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Selective Hydrogenation of Aromatic Ketones and Phenols
by CAAC-Rhodium Complexes
Department of chemistry
Indian Institute of Technology
New Delhi, 110016
Presented by
HAMIT
2021CYS7021
The stability of aromatic hydrocarbons due to aromaticity is likely why polar carbonyls
are better substrates for hydrogenation than aromatic hydrocarbons. As a result, aryl-
containing alcohols are usually produced by the hydrogenation of aromatic ketones via
a preferred carbonyl reduction.
? ?
For selective arene hydrogenation takes place over ketone hydrogenation a proper catalyst is required which
facilitates interaction with the aryl group via 𝜋 - coordination. For that purpose, electron-rich CAAC ligands
are found to be useful they have strong donation to metal which increases the interaction of the metal with
aryl. This is due to an increase in the electron density of metal which facilitates back-donation of electron
density to the empty 𝜋* antibonding orbital of aryl from metal’s filled d orbitals. This might benefit the
hydrogenation of arene with H2 and also metals show low oxophilicity due to an increase in electron density.
Rhodium is the best transition metal as compared to others towards arene hydrogenation over ketone
hydrogenation.
Selective Hydrogenation of Aromatic Ketones
Preparation of the CAAC-Rh complex was done in two steps, firstly CAAC●HX reacts with the base then
the resulting carbene reacts with [Rh(COD)Cl]2.
In a solvent mixture of trifluoroethanol and water (ratio of 19:1), the (CAAC-1)Rh- (COD)Cl
complex exhibits strong reactivity for phenol hydrogenation, exclusively yielding the product.
By selectively reducing the aryl scaffolds while keeping functional carbonyl groups, an
effective CAAC-Rh catalyst is useful for the hydrogenation of aromatic ketones and
phenols into cyclohexyl-containing ketones and cyclohexanones. By using rhodium
complexes with the electronic structural characteristics of CAAC ligands, it is possible to
significantly increase selectivity and also achieve high compatibility with a variety of
C=O-containing structural including esters, carboxylic acids, ketones, amides, and amino
acids.
Selective Hydrogenation of Aromatic Ketones and Phenols using CAAC-Rhodium Complexes

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Selective Hydrogenation of Aromatic Ketones and Phenols using CAAC-Rhodium Complexes

  • 1. Selective Hydrogenation of Aromatic Ketones and Phenols by CAAC-Rhodium Complexes Department of chemistry Indian Institute of Technology New Delhi, 110016 Presented by HAMIT 2021CYS7021
  • 2. The stability of aromatic hydrocarbons due to aromaticity is likely why polar carbonyls are better substrates for hydrogenation than aromatic hydrocarbons. As a result, aryl- containing alcohols are usually produced by the hydrogenation of aromatic ketones via a preferred carbonyl reduction.
  • 3. ? ?
  • 4. For selective arene hydrogenation takes place over ketone hydrogenation a proper catalyst is required which facilitates interaction with the aryl group via 𝜋 - coordination. For that purpose, electron-rich CAAC ligands are found to be useful they have strong donation to metal which increases the interaction of the metal with aryl. This is due to an increase in the electron density of metal which facilitates back-donation of electron density to the empty 𝜋* antibonding orbital of aryl from metal’s filled d orbitals. This might benefit the hydrogenation of arene with H2 and also metals show low oxophilicity due to an increase in electron density. Rhodium is the best transition metal as compared to others towards arene hydrogenation over ketone hydrogenation. Selective Hydrogenation of Aromatic Ketones
  • 5.
  • 6. Preparation of the CAAC-Rh complex was done in two steps, firstly CAAC●HX reacts with the base then the resulting carbene reacts with [Rh(COD)Cl]2.
  • 7. In a solvent mixture of trifluoroethanol and water (ratio of 19:1), the (CAAC-1)Rh- (COD)Cl complex exhibits strong reactivity for phenol hydrogenation, exclusively yielding the product.
  • 8. By selectively reducing the aryl scaffolds while keeping functional carbonyl groups, an effective CAAC-Rh catalyst is useful for the hydrogenation of aromatic ketones and phenols into cyclohexyl-containing ketones and cyclohexanones. By using rhodium complexes with the electronic structural characteristics of CAAC ligands, it is possible to significantly increase selectivity and also achieve high compatibility with a variety of C=O-containing structural including esters, carboxylic acids, ketones, amides, and amino acids.