Selective C(sp3)−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow. Issue 15 (12th March 2018)

• Record Type: Journal Article
• Authors: Laudadio, Gabriele; Govaerts, Sebastian; Wang, Ying; Ravelli, Davide; Koolman, Hannes F.; Fagnoni, Maurizio; Djuric, Stevan W.; Noël, Timothy
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 15(2018)
• Page Start: 4078
• Page End: 4082
• Publication Date: 2018-03-12
• Subjects: aerobic oxidation -- C(sp3)−H functionalization -- decatungstate -- flow chemistry -- photocatalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201800818
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A mild and selective C(sp 3 )−H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both activated and unactivated C−H bonds (30 examples). The ability to selectively oxidize natural scaffolds, such as (−)‐ambroxide, pregnenolone acetate, (+)‐sclareolide, and artemisinin, exemplifies the utility of this new method. Abstract : Good clean functionalization : A mild and selective C(sp 3 )−H oxidation promoted by an inexpensive decatungstate photocatalyst was significantly improved by a microflow reactor, which enabled the safe use of oxygen and enhanced irradiation of the reaction mixture. Both activated and unactivated C−H bonds could be oxidized by this sustainable method, including those in natural scaffolds, such as (−)‐ambroxide and artemisinin.