4.8 Article

C(sp3)-H bond functionalization with styrenes via hydrogen-atom transfer to an aqueous hydroxyl radical under photocatalysis

Journal

GREEN CHEMISTRY
Volume 23, Issue 10, Pages 3575-3580

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1gc00753j

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Funding

  1. Asahi Glass Foundation - MEXT [18H04247]
  2. Grants-in-Aid for Scientific Research [18H04247] Funding Source: KAKEN

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The study introduces a novel method for the redox-neutral addition of alpha-C-H bonds of acetonitrile and acetone to styrenes, enabled by the hydrogen-atom transfer from relatively acidic and water-miscible C(sp(3))-H bonds to an aqueous hydroxyl radical generated cleanly and iteratively by the oxidation of water under silver-nanoparticle-loaded titania photocatalysis without using stoichiometric oxidation agents.
The redox-neutral addition of alpha-C-H bonds of acetonitrile and acetone to styrenes was enabled via the hydrogen-atom transfer from relatively acidic and water-miscible C(sp(3))-H bonds to an aqueous hydroxyl radical generated cleanly and iteratively by the oxidation of water under silver-nanoparticle-loaded titania photocatalysis without using stoichiometric oxidation agents.

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