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Synfacts 2020; 16(09): 1127
DOI: 10.1055/s-0040-1705827
Flow Chemistry

C–H Activation of Gaseous Alkanes

Contributor(s):
Paul Knochel
,
Ferdinand H. Lutter
Laudadio G, Deng Y, van der Wal K, Ravelli D, Nuño M, Fagnoni M, Guthrie D, Sun Y, Noël T. * Eindhoven University of Technology, The Netherlands
C(sp3)–H Functionalizations of Light Hydrocarbons using Decatungstate Photocatalysis in Flow.

Science 2020;
369: 92-96
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Key words

photocatalysis - C–H functionalization - hydrocarbons

Significance

Noël and co-workers describe a photocatalytic C–H activation of gaseous alkanes and subsequent trapping with various Michael acceptors in continuous flow. The corresponding alkylated products were obtained in moderate to excellent yields.


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Comment

Mechanistically, the authors propose an initial activation of the photocatalyst TBADT, which relaxes to its active form wO. A hydrogen abstraction forms a carbon-centered radical, which undergoes a 1,4-addition to a Michael acceptor. Hydrogen back-donation affords the alkylated product and regenerates the catalyst.


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Publication History

Article published online:
18 August 2020

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