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. 2018 Apr 3;57(15):4078-4082.
doi: 10.1002/anie.201800818. Epub 2018 Mar 12.

Selective C(sp3 )-H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow

Gabriele Laudadio  1 , Sebastian Govaerts  1 , Ying Wang  2 , Davide Ravelli  3 , Hannes F Koolman  2   4 , Maurizio Fagnoni  3 , Stevan W Djuric  2 , Timothy Noël  1
Affiliations

Selective C(sp3 )-H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow

Gabriele Laudadio et al. Angew Chem Int Ed Engl. .

Abstract

A mild and selective C(sp3 )-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.

Keywords: C(sp3)−H functionalization; aerobic oxidation; decatungstate; flow chemistry; photocatalysis.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
a) Transition‐metal‐catalyzed C(sp3)−H oxidation strategies. b) Electrochemical C(sp3)−H oxidation. c) Our strategy for selective C(sp3)−H aerobic oxidation enabled by decatungstate photocatalysis in flow.
Scheme 2
Scheme 2
Scope of the C(sp3)−H oxidation enabled by decatungstate photocatalysis in flow. The oxidation site is indicated in gray and with an asterisk, unless otherwise noted. [a] The yield was determined by GC. [b] The reaction was carried out in the absence of 1 m HCl. [c] The reaction was carried out with CH3CN/dichloromethane (2.5:1) as the solvent. [d] The reaction was carried out with a residence time of 1.5 h. Boc=tert‐butoxycarbonyl.
See this image and copyright information in PMC

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