Bi(OTf)<sub>3</sub>-Catalyzed Cascade Cycloaddition–Decarbonylation–<i>N</i>-Deoxygenative Aromatization between 2-Arylisatogens and Styrenes: Unveiling a Synthesis of 2,4-Diarylquinolines
An unprecedented Bi(OTf)<sub>3</sub>-catalyzed reaction between 2-arylisatogens and vinylarenes to yield 2,4-diarylquinolines is reported. The transformation occurred via a Bi<sup>III</sup>-coordination to the embedded anionic nitrone oxygen, which induced a regiospecific stepwise formal [4 + 2]-cycloaddition with vinylarenes to yield a strained tricyclic intermediate, which subsequently extruded gaseous carbon monoxide. <i>N</i>-Deoxygenative aromatization ensued to produce 2,4-diarylquinolines. The protocol was applicable to a variety of substrates to produce the quinolines in up to an 89% yield.
Authors
- Jumreang Tummatorn (ORCID: https://orcid.org/0000-0002-1662-151X)
- Somsak Ruchirawat (ORCID: https://orcid.org/0000-0001-5842-4330)
- Charnsak Thongsornkleeb (ORCID: https://orcid.org/0000-0003-2653-5137)
- Kunlayanee Punjajom (ORCID: https://orcid.org/0000-0001-7296-6689)
- Sukit Chonradeenitchakul
Institutions
- Chulabhorn Graduate Institute (TH)
- Chulabhorn Research Institute (TH)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-15
- DOI
- https://doi.org/10.1021/acs.orglett.4c03012
- Citations
- 12
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.00
Funders
- Chulabhorn Royal Academy
- National Research Council of Thailand
- Chulabhorn Research Institute
- Ministry of Higher Education, Science, Research and Innovation, Thailand
- Thailand Science Research and Innovation
- Chulabhorn Graduate Institute, Chulabhorn Royal Academy