Optimization of a Decatungstate-Catalyzed C(sp3)–H Alkylation Using a Continuous Oscillatory Millistructured Photoreactor

Zhenghui Wen, A. Maheshwari, Carlo Sambiagio, Yuchao Deng, Gabriele Laudadio, Koen Van Aken, Yuhan Sun, H.P.L. Gemoets, Timothy Noël (Corresponding author)

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Tetrabutylammonium decatungstate (TBADT) has emerged as an efficient and versatile photocatalyst for hydrogen atom transfer (HAT) processes that enables the cleavage of both activated and unactivated aliphatic C–H bonds. Using a recently developed oscillatory millistructured continuous-flow photoreactor, investigations of a decatungstate-catalyzed C(sp3)–H alkylation protocol were carried out, and the results are presented here. The performance of the reactor was evaluated in correlation to several chemical and process parameters, including residence time, light intensity, catalyst loading, and substrate/reagent concentration. In comparison with previously reported batch and flow protocols, conditions were found that led to considerably higher productivity, achieving a throughput up to 36.7 mmol/h with a residence time of only 7.5 min.
Original languageEnglish
Pages (from-to)2356-2361
Number of pages6
JournalOrganic Process Research & Development
Issue number10
Early online date2020
Publication statusPublished - 16 Oct 2020


Z.W. and Y.D. acknowledge support from the China Scholarship Council (CSC). C.S. acknowledges the European Union for a Marie Curie European Postdoctoral Fellowship (FlowAct, Grant 794072). G.L. acknowledges financial support from the Dutch Science Foundation (NWO) for a VIDI Grant for T.N. (SensPhotoFlow, 14150). Finally, the authors acknowledge support from COST Action CA15106 (C–H Activation in Organic Synthesis, CHAOS). We thank Creaflow and Ajinomoto Bio-Pharma Services for the use of the HANU reactor and the irradiation source.

FundersFunder number
Horizon 2020 Framework Programme794072
European Commission
European Cooperation in Science and Technology (COST)CA15106
Nederlandse Organisatie voor Wetenschappelijk Onderzoek14150
China Scholarship Council


    • C-H functionalization
    • decatungstate
    • flow photochemistry
    • hydrogen atom transfer
    • photocatalysis
    • process intensification


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