Work

Bi(OTf)3-Catalyzed Cascade Cycloaddition–Decarbonylation–N-Deoxygenative Aromatization between 2-Arylisatogens and Styrenes: Unveiling a Synthesis of 2,4-Diarylquinolines

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide An unprecedented Bi(OTf) 3 -catalyzed reaction between 2-arylisatogens and vinylarenes to yield 2,4-diarylquinolines is reported. The transformation occurred via a Bi III -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. N -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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c03012

Authors: Kunlayanee Punjajom, Sukit Chonradeenitchakul, Jumreang Tummatorn, Somsak Ruchirawat, Charnsak Thongsornkleeb

Institutions: Chulabhorn Graduate Institute, Chulabhorn Research Institute, Ministry of Higher Education, Science, Research and Innovation

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500