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Decatungstate-Mediated C(sp )-H Heteroarylation via Radical-Polar Crossover in Batch and Flow. | LitMetric

Decatungstate-Mediated C(sp )-H Heteroarylation via Radical-Polar Crossover in Batch and Flow.

Angew Chem Int Ed Engl

Flow Chemistry Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands.

Published: August 2021

AI Article Synopsis

  • - Photocatalytic hydrogen atom transfer is an effective method for efficiently modifying organic molecules with specific focus on C(sp)-H functionalization.
  • - This study introduces a novel approach that combines decatungstate photocatalysis with radical-polar crossover to facilitate direct oxidative C(sp)-H heteroarylation.
  • - The new method exhibits a high tolerance for various functional groups and is scalable using continuous-flow reactors, making it suitable for modifying complex biologically relevant compounds.

Article Abstract

Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp )-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 net-oxidative C(sp )-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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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8457183PMC
http://dx.doi.org/10.1002/anie.202104682DOI Listing

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