It is here reported a fully sustainable and generally applicable protocol for the regioselective hydroformylation of terminal alkenes, using cheap commercially available catalysts and ligands, in mild reaction conditions (70 °C, 9 bar, 40 min). The process can take advantages from both micellar catalysis and microwave irradiation to obtain the linear aldehydes as the major or sole regioisomers in good to high yields. The substrate scope is largely explored as well as the application of hydroformylation in tandem with intramolecular hemiacetalization thus demonstrating the compatibility with a broad variety of functional groups. The reaction is efficient even in large scale and the catalyst and micellar water phase can be reused at least 5 times without any impact in reaction yields. The efficiency and sustainability of this protocol is strictly related to the in situ transformation of the aldehyde into the corresponding Bertagnini’s salt that precipitates in the reaction mixture avoiding organic solvent mediated purification steps to obtain the final aldehydes as pure compounds.

Migliorini, F., Dei, F., Maramai, S., Calamante, M., Petricci, E. (2021). Micellar catalysis for sustainable hydroformylation. CHEMCATCHEM, 13(12), 2794-2806 [10.1002/cctc.202100181].

Micellar catalysis for sustainable hydroformylation

F. Migliorini
Membro del Collaboration Group
;
S. Maramai
Membro del Collaboration Group
;
E. Petricci
Membro del Collaboration Group
2021-01-01

Abstract

It is here reported a fully sustainable and generally applicable protocol for the regioselective hydroformylation of terminal alkenes, using cheap commercially available catalysts and ligands, in mild reaction conditions (70 °C, 9 bar, 40 min). The process can take advantages from both micellar catalysis and microwave irradiation to obtain the linear aldehydes as the major or sole regioisomers in good to high yields. The substrate scope is largely explored as well as the application of hydroformylation in tandem with intramolecular hemiacetalization thus demonstrating the compatibility with a broad variety of functional groups. The reaction is efficient even in large scale and the catalyst and micellar water phase can be reused at least 5 times without any impact in reaction yields. The efficiency and sustainability of this protocol is strictly related to the in situ transformation of the aldehyde into the corresponding Bertagnini’s salt that precipitates in the reaction mixture avoiding organic solvent mediated purification steps to obtain the final aldehydes as pure compounds.
2021
Migliorini, F., Dei, F., Maramai, S., Calamante, M., Petricci, E. (2021). Micellar catalysis for sustainable hydroformylation. CHEMCATCHEM, 13(12), 2794-2806 [10.1002/cctc.202100181].
File in questo prodotto:
File Dimensione Formato  
cctc.202100181 (2).pdf

accesso aperto

Descrizione: Articolo
Tipologia: PDF editoriale
Licenza: Creative commons
Dimensione 3.07 MB
Formato Adobe PDF
3.07 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/1152224