Community Research and Development Information Service - CORDIS

FP7

HYDROACYLATION Result In Brief

Project ID: 328996
Funded under: FP7-PEOPLE
Country: United Kingdom

Hydroacylation raises its catalytic profile

From the industrial solvent propanone or acetone to a stunning range of chemicals for further transformation, alkanones are a valuable component of the organic chemical industry. Thanks to EU research, catalytic conversion to a ketone is about to become more efficient.
Hydroacylation raises its catalytic profile
Hydroacylation (HA) is a powerful transformation process in the organic synthesis world. The transformation of an aldehyde and an unsaturated hydrocarbon into a ketone, HA involves the formation of a new C-C bond. The most common catalysts used are rhodium-based. Although this occurs under atom-economical conditions, there is a possibility of decarbonylation (loss of a C=O) from one of the reaction intermediate compounds.

The HYDROACYLATION (Rhodium-catalyzed alkene and alkyne hydroacylation) project has synthesised a new family of rhodium complexes with small bite angle, hemilable diphosphine ligands. Previous research by the group has shown that the small bite angle of the complex and hemilable ligands accelerate the main reaction.

Researchers tested the new catalysts using a wide range of inactivated alkenes with β-substituted aldehydes. The complexes were excellent catalysts for intermolecular hydroacylation and showed resistance to decarbonylation, enabling substrate recharge without loss in conversion.

The team were able to collect data on rate and order using labelling studies. The mechanistic studies showed exactly why the novel catalysts were superior in terms of activity and selectivity.

The HYDROACYLATION project has produced a set of HA catalysts with high levels of functional group tolerance, stability under catalytic conditions, attractive rates of reaction for demanding substrates and low catalyst concentration using minimal and green solvents. The HA process will be able to replace other synthetic reactions in the organic chemical industry. The result will be the cost-effective production of fine and bulk chemicals, new materials and target molecules.

Related information

Keywords

Hydroacylation, alkanone, catalytic conversion, rhodium, decarbonylation, bite angle, diphosphine ligand
Record Number: 188390 / Last updated on: 2016-08-30
Domain: Biology, Medicine