Skip to content
DraconiticResearch
Search Sources API
194,164 studies31 sourcesUpdated 48 min ago
PreprintCC BY-NC-NDChemRxiv

Remote C(sp3)–H Functionalization via Visible-Light-Mediated Generation of Amidyl Radicals from Readily Accessible Arylsulfonamides

  • Kippei Hirao1,2
  • Masashi Okamoto3,4,5,2
  • Mai Fukuda1,2
  • Yuya Komatani5,2
  • Norihito Arichi3,4
  • Hiroaki Ohno3,4
  • Shinsuke Inuki3,4,5,2,6
6 affiliations
  1. 1Faculty of Pharmaceutical Sciences
  2. 2Tokushima University
  3. 3Graduate School of Pharmaceutical Sciences
  4. 4Kyoto University
  5. 5Graduate School of Biomedical Sciences
  6. 6Institute of Photonics and Human Health Frontier
Open at sourcePDFDOICite

Abstract

Remote C(sp3)–H functionalization via amidyl radical-mediated 1,5-hydrogen atom transfer has emerged as a powerful strategy for the synthesis and late-stage modification of structurally complex molecules. However, practical methods for amidyl radical generation that combine easily prepared precursors with mild reaction conditions remain highly desirable. Herein, we report a visible-light-mediated method for generating amidyl radicals from readily accessible arylsulfonamides through precise tuning of the reduction potential of the arylsulfonyl group. Systematic evaluation of arylsulfonyl groups identified the benzothiazolesulfonyl group as an efficient precursor for amidyl radical generation. The reaction exhibited broad substrate scope, including for amino acid and peptide derivatives, and was readily applicable to continuous-flow synthesis. Mechanistic studies support a pathway involving single-electron transfer from the photocatalyst and provide insight into the roles of additives in product formation.

Related

  1. Neutral photogenerated N-centred radicals as a general, catalytic direct hydrogen atom transfer platform for aliphatic C–H functionalization
    Boya Feng, Mattia Lepori, Michał Domański +9
    Nature CatalysisPeer-reviewedCC BYFull text9 citedOrganic chemistryOpenAlex
  2. A General Approach for the Generation of alpha-Thioalkyl Radicals from Pinacol Boronic Ester Precursors
    Lise Benoist, Fabrice Dénès, Philippe Renaud
    ChemRxivPreprintLicence not statedGeneral chemistryChemRxiv
  3. Red light mediated energy transfer catalysis via stable organic radicals
    Tzu-Hsuan Feng, Ana Paula Nita Vizcardo, Andrew Brian Pun
    Chemical SciencePeer-reviewedCC BY 3.0Full textOrganic chemistryPMC
  4. Functionalization‐Mediated Synthesis of Bridge‐Coordinated Fe Atoms on MoS ₂ Nanosheets for PEM Water Electrolyzers
    Zakaria Anfar, Haitham Maslouh, Yuwei Yang +11
    Angewandte Chemie International EditionPeer-reviewedCC BY 4.0Full text1 citedElectrochemistry & energyHAL
  5. Supramolecular Mask-Mediated Regioselective bis-Bingel-Functionalization of M3N@Ih-C80 (M = Lu, Sc).
    Valentina Iannace, Clara Sabrià, Sheng Zhu +10
    Journal of the American Chemical SocietyPeer-reviewedCC BYFull textOrganic chemistryEurope PMCPMC

Cite

BibTeXRIS
BibTeX
@misc{hirao2026remote,
  title = {{Remote C(sp3)–H Functionalization via Visible-Light-Mediated Generation of Amidyl Radicals from Readily Accessible Arylsulfonamides}},
  author = {Kippei Hirao and Masashi Okamoto and Mai Fukuda and Yuya Komatani and Norihito Arichi and Hiroaki Ohno and Shinsuke Inuki},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15008393/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008393/v1},
  note = {CC BY-NC-ND},
}
RIS
TY  - UNPB
TI  - Remote C(sp3)–H Functionalization via Visible-Light-Mediated Generation of Amidyl Radicals from Readily Accessible Arylsulfonamides
AU  - Kippei Hirao
AU  - Masashi Okamoto
AU  - Mai Fukuda
AU  - Yuya Komatani
AU  - Norihito Arichi
AU  - Hiroaki Ohno
AU  - Shinsuke Inuki
PY  - 2026
DA  - 2026/09/07
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15008393/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008393/v1
AB  - Remote C(sp3)–H functionalization via amidyl radical-mediated 1,5-hydrogen atom transfer has emerged as a powerful strategy for the synthesis and late-stage modification of structurally complex molecules. However, practical methods for amidyl radical generation that combine easily prepared precursors with mild reaction conditions remain highly desirable. Herein, we report a visible-light-mediated method for generating amidyl radicals from readily accessible arylsulfonamides through precise tuning of the reduction potential of the arylsulfonyl group. Systematic evaluation of arylsulfonyl groups identified the benzothiazolesulfonyl group as an efficient precursor for amidyl radical generation. The reaction exhibited broad substrate scope, including for amino acid and peptide derivatives, and was readily applicable to continuous-flow synthesis. Mechanistic studies support a pathway involving single-electron transfer from the photocatalyst and provide insight into the roles of additives in product formation.
ER  -