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PreprintCC BY-NC-NDChemRxiv

Lewis Acid-Activated Bathophenanthroline Photoredox System for Chlorine Radical-Mediated C(sp³)–H Alkylation

  • Naoki Oku1,2
  • Akane Tomita1,2
  • Tomoya Miura1,2
  1. 1Division of Applied Chemistry
  2. 2Okayama University
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Abstract

Despite major advances in photoredox catalysis, photocatalysts capable of oxidizing substrates with E ox > +2.0 V vs SCE remain limited. Herein, we report that a Lewis acid-activated bathophenanthroline (bphen) photoredox system with ZrCl 4 enables intermolecular single-electron oxidation of chloride ( E ox = +2.03 V vs SCE). Under visible-light irradiation, this system promotes Giese-type alkylation of electron-deficient alkenes with a broad range of C(sp 3 )–H donors through chlorine radical-mediated hydrogen atom transfer (HAT). Detailed spectroscopic, electrochemical, kinetic, and computational studies reveal that Lewis acid activation of bphen enhances the excited-state oxidizing power and enables the intermolecular oxidation of chloride to generate a chlorine radical.

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Cite

BibTeXRIS
BibTeX
@misc{oku2026lewis,
  title = {{Lewis Acid-Activated Bathophenanthroline Photoredox System for Chlorine Radical-Mediated C(sp³)–H Alkylation}},
  author = {Naoki Oku and Akane Tomita and Tomoya Miura},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010834/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010834/v1},
  note = {CC BY-NC-ND},
}
RIS
TY  - UNPB
TI  - Lewis Acid-Activated Bathophenanthroline Photoredox System for Chlorine Radical-Mediated C(sp³)–H Alkylation
AU  - Naoki Oku
AU  - Akane Tomita
AU  - Tomoya Miura
PY  - 2026
DA  - 2026/10/22
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010834/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010834/v1
AB  - Despite major advances in photoredox catalysis, photocatalysts capable of oxidizing substrates with E ox > +2.0 V vs SCE remain limited. Herein, we report that a Lewis acid-activated bathophenanthroline (bphen) photoredox system with ZrCl 4 enables intermolecular single-electron oxidation of chloride ( E ox = +2.03 V vs SCE). Under visible-light irradiation, this system promotes Giese-type alkylation of electron-deficient alkenes with a broad range of C(sp 3 )–H donors through chlorine radical-mediated hydrogen atom transfer (HAT). Detailed spectroscopic, electrochemical, kinetic, and computational studies reveal that Lewis acid activation of bphen enhances the excited-state oxidizing power and enables the intermolecular oxidation of chloride to generate a chlorine radical.
ER  -