Visible-Light-Induced <i>ortho</i>-Quinone Methides Formation in Situ Using <i>ortho</i>-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction
Reported herein is the generation of <i>ortho</i>-quinone methides (<i>o</i>-QMs) via metal-free visible-light-induced oxidation of <i>ortho</i>-alkylarenols, as well as their subsequent reaction with olefins to afford chromans in good to excellent yields (up to 91%). The key is the selective activation of the benzylic C(sp<sup>3</sup>)-H bond of <i>ortho</i>-alkylarenols via single electron transfer (SET) and the formation of <i>o</i>-QMs via hydrogen atom transfer (HAT).
Authors
- Wang Shu (ORCID: https://orcid.org/0000-0001-7982-6398)
- Zhiyuan Huang (ORCID: https://orcid.org/0000-0003-4180-0234)
- Chen‐Ho Tung (ORCID: https://orcid.org/0000-0001-9999-9755)
- Li‐Zhu Wu (ORCID: https://orcid.org/0000-0002-5561-9922)
- Cheng Wang (ORCID: https://orcid.org/0000-0002-1834-2119)
- Liang Ge (ORCID: https://orcid.org/0009-0005-0976-8168)
- Chenhong Wang (ORCID: https://orcid.org/0000-0003-4272-435X)
Institutions
- Chinese Academy of Sciences (CN)
- Technical Institute of Physics and Chemistry (CN)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-26
- DOI
- https://doi.org/10.1021/acs.orglett.4c04494
- Citations
- 4
- Primary Topic
- Synthesis of Indole Derivatives
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- Beijing Municipal Natural Science Foundation
- National Key Research and Development Program of China