Aerobic Baeyer–Villiger Oxidation Catalyzed by a Flavin‐Containing Enzyme Mimic in Water. Issue 50 (14th November 2018)

• Record Type: Journal Article
• Authors: Chevalier, Yoan; Lock Toy Ki, Yvette; le Nouen, Didier; Mahy, Jean‐Pierre; Goddard, Jean‐Philippe; Avenier, Frédéric
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 50(2018)
• Page Start: 16412
• Page End: 16415
• Publication Date: 2018-11-14
• Subjects: Baeyer–Villiger reaction -- enzymes -- oxidation -- oxygen heterocycles -- sustainable chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201810124
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Direct incorporation of molecular oxygen into small organic molecules has attracted much attention for the development of new environmentally friendly oxidation processes. In line with this approach, bioinspired systems mimicking enzyme activities are of particular interest since they may perform catalysis in aqueous media. Demonstrated herein is the incorporation of a natural flavin cofactor (FMN) into the specific microenvironment of a water‐soluble polymer which allows the efficient reduction of the FMN by NADH in aqueous solution. Once reduced, this artificial flavoenzyme can then activate molecular dioxygen under aerobic conditions and result in the Baeyer–Villiger reaction at room temperature in water. Abstract : Keeping it local : Incorporation of flavin cofactors (FMN) within the local hydrophobic microenvironment of a modified polyethyleneimine allows activation of dioxygen in the presence of NADH. This activation results in a successful Baeyer–Villiger reaction at room temperature in water.