Synthesis 2025; 57(20): 2963-2968
DOI: 10.1055/a-2630-0528
Paper
Published as part of the Special Topic Water in Organic Reactions

“On-water” Photochemical Thiol-Ene Reaction of N-Enoxybenzotriazoles

Authors

  • Jong In Jung

    1   Department of Chemistry, Hanyang University, Seoul, Republic of Korea
  • Jun Sup Lee

    1   Department of Chemistry, Hanyang University, Seoul, Republic of Korea
    2   Process Chemistry Department, Yuhan R&D Institute, Yong-In, Republic of Korea
  • Seunghoon Shin

    1   Department of Chemistry, Hanyang University, Seoul, Republic of Korea

Supported by: Korea Drug Development Fund RS-2023-00259634
Supported by: National Research Foundation of Korea NRF-2021R1A2C3010552
Funding Information We thank National Research Foundation of Korea (NRF-2021R1A2C3010552) and the Korea Drug Development Fund (RS-2023-00259634) for generous support.


Graphical Abstract

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Abstract

We report herein a photochemical thiol-ene coupling using N-enoxybenzotriazoles, significantly accelerated under “on-water” conditions. This approach achieves efficient coupling within just five minutes via a remarkably rapid radical chain reaction, attributed to enhanced EDA formation and accelerated radical addition through a hydrophobic effect. The robustness of this method under various perturbation conditions underscores its potential for broad applications.

Supplementary Material



Publication History

Received: 26 April 2025

Accepted after revision: 06 June 2025

Accepted Manuscript online:
06 June 2025

Article published online:
01 August 2025

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