Photocatalyzed hydrogen atom transfer enables multicomponent olefin oxo-amidomethylation under aerobic conditions

Lepori, Mattia and Ioannou, Dimitris I. and Barham, Joshua P. and Noël, Timothy (2025) Photocatalyzed hydrogen atom transfer enables multicomponent olefin oxo-amidomethylation under aerobic conditions. Chemical Science, 16 (48). pp. 22944-22951. ISSN 2041-6539 (https://doi.org/10.1039/d5sc06277b)

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Abstract

The direct functionalization of abundant and readily available feedstock chemicals has emerged as a powerful strategy to rapidly increase molecular complexity and access valuable scaffolds. Herein, we report a novel photocatalyzed three-component oxo-amidomethylation of aromatic olefins under aerobic conditions, enabling the synthesis of N-(g-oxopropyl)amides via simultaneous incorporation of two orthogonal functional groups across the alkene C]C bond in a single step. Mechanistic features include the photocatalyzed hydrogen atom transfer (HAT)-mediated engagement of the a-N-alkyl C(sp3)–H bond in inexpensive, unfunctionalized amide feedstocks and the trapping of a key olefinderived carbon-centered radical intermediate by molecular oxygen to afford the oxo-functionalized homologated products. This cascade protocol demonstrates compatibility with a broad range of aryl olefins and amides, as well as efficient scalability. The method provides streamlined access to high-value molecular architectures of synthetic and pharmaceutical relevance without the need for prefunctionalized radical precursors.

ORCID iDs

Barham, Joshua P. ORCID: https://orcid.org/0000-0003-1675-9399

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• Item metadata

  Item type:	Article
  ID code:	94883
  Dates:	Date Event 28 December 2025 Published 18 November 2025 Published Online 17 November 2025 Accepted 17 August 2025 Submitted
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	04 Dec 2025 13:07
  Last modified:	12 Feb 2026 08:58
  URI:	https://strathprints.strath.ac.uk/id/eprint/94883