Highly chemoselective and regiospecific Rh-catalyzed single-step hydroformylation of biomass derived (R)-carvone

• Use of the bio-renewable olefin , (R)-carvone makes the hydroformylation process sustainable. • The system is extremely sensitive to changes in the reaction conditions which necessitates rigorous optimizations. • Employment of Rh/Xantphos catalytic system leads to an aldehyde favoring approach. • Selectivity tuning gives 99 % conversion, 95 % yield and 96 % chemoselectivity toward the desired aldehyde under optimized conditions. • The formation of only the linear aldehyde makes the system regiospecific. An efficient protocol for the rhodium catalyzed single-step hydroformylation of renewable natural olefin , (R)-carvone was developed, obtaining the corresponding linear aldehyde as the major product. The system was found to be highly sensitive to even slight variations in the reaction conditions, which had a tendency to complicate itself through the formation of numerous byproducts; nonetheless, high conversion (99 %), yield (95 %) and chemoselectivity (96 %) toward the desired aldehyde were accomplished under the optimized conditions. Moreover, this process proved to be regiospecific as no branched aldehyde was formed. These results were achieved by a careful tuning of different parameters such as temperature, pressure, reaction time, catalyst to ligand ratio, catalyst to substrate ratio and types of catalyst precursors, ligands and solvents.

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Publication Details

Journal
Molecular Catalysis
Published
2024-10-13
DOI
https://doi.org/10.1016/j.mcat.2024.114607
Citations
5
Primary Topic
Microbial Metabolic Engineering and Bioproduction
Type
article
Field-Weighted Citation Impact
1.17

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article

Highly chemoselective and regiospecific Rh-catalyzed single-step hydroformylation of biomass derived (R)-carvone

Bhalchandra Mahadeo Bhanage, Rupali S. Prajapati
5 citations
Molecular Catalysis
Microbial Metabolic Engineering and Bioproduction
1.17
article

Highly chemoselective and regiospecific Rh-catalyzed single-step hydroformylation of biomass derived (R)-carvone

Bhalchandra Mahadeo Bhanage, Rupali S. Prajapati
article en
5 citations

Abstract

• Use of the bio-renewable olefin , (R)-carvone makes the hydroformylation process sustainable. • The system is extremely sensitive to changes in the reaction conditions which necessitates rigorous optimizations. • Employment of Rh/Xantphos catalytic system leads to an aldehyde favoring approach. • Selectivity tuning gives 99 % conversion, 95 % yield and 96 % chemoselectivity toward the desired aldehyde under optimized conditions. • The formation of only the linear aldehyde makes the system regiospecific. An efficient protocol for the rhodium catalyzed single-step hydroformylation of renewable natural olefin , (R)-carvone was developed, obtaining the corresponding linear aldehyde as the major product. The system was found to be highly sensitive to even slight variations in the reaction conditions, which had a tendency to complicate itself through the formation of numerous byproducts; nonetheless, high conversion (99 %), yield (95 %) and chemoselectivity (96 %) toward the desired aldehyde were accomplished under the optimized conditions. Moreover, this process proved to be regiospecific as no branched aldehyde was formed. These results were achieved by a careful tuning of different parameters such as temperature, pressure, reaction time, catalyst to ligand ratio, catalyst to substrate ratio and types of catalyst precursors, ligands and solvents.

Molecular CatalysisVol. 569
Institute of Chemical Technology (IN)
Department of Science and Technology, Ministry of Science and Technology, India, University Grants Commission
Openalex Percentile: Top 21%
Microbial Metabolic Engineering and Bioproduction
1.17
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