Decatungstate-mediated C(sp3 )‒H Heteroarylation via Radical Polar Crossover in Batch and Flow
- Ting Wana
- Luca Capaldoa
- Gabriele Laudadioa
- Alexander V. Nyuchevb
- Juan A. Rincónc
- Pablo García-Losadac
- Carlos Mateosc
- Michael O. Frederickd
- Manuel Nuñoe
- Timothy Noël*a
- aFlow Chemistry Group, Van ’t Hoff Institute for Molecular Sciences(HIMS), University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands
- bDepartment of Organic Chemistry, Lobachevsky State University of Nizhny Novgorod Gagarina Avenue 23, 603950, Nizhny Novgorod, Russia
- cCentro de Investigación Lilly S.A. Avda. de la Industria 30, Alcobendas-Madrid 28108, Spain.
- dSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, United States.
- eVapourtec Ltd., Park Farm Business Centre, Fornham St Genevieve, Bury St Edmunds, Suffolk IP28 6TS, United Kingdom.Read the publication that featured this abstract
Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp3)‒H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstate hydrogen atom transfer photocatalysis with the oxidative Radical-Polar Crossover concept to access the direct netoxidative C(sp3)‒H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuous-flow reactor technology. The developed protocol is also amenable to the late-stage functionalization of biologically relevant molecules such as stanozolol, (‒)-ambroxide, podophyllotoxin and dideoxyribose.
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