Micellar Catalysis for Sustainable Hydroformylation. Issue 12 (5th May 2021)

• Record Type: Journal Article
• Authors: Migliorini, Francesca; Dei, Filippo; Calamante, Massimo; Maramai, Samuele; Petricci, Elena
• Is Part Of: ChemCatChem. Volume 13:Issue 12(2021)
• Page Start: 2794
• Page End: 2806
• Publication Date: 2021-05-05
• Subjects: Hydroformylation -- micellar catalysis -- microwave -- cyclic acetals; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.202100181
• Languages: English
• ISSNs: 1867-3880

Abstract

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. Abstract : Without purifications : 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 was developed. The process can take advantages from both micellar catalysis and microwave irradiation to obtain the linear aldehydes as the major or sole regioisomers in high yields. The reaction is efficient even in large scale the catalyst and micellar water phase being reused at least 5 times without any impact in reaction yields.