Tandem S<sub>N</sub>Ar/Aldol Condensation of Oxindoles with <i>o</i>-Haloacetophenones Enables Modular Assembly of 2,3-Fused Indolines Bearing a Quaternary Carbon
Described herein is a novel base-promoted [4 + 2] annulation reaction of 3-methyl-indolin-2-ones with <i>ortho</i>-haloacetophenones, which enables the modular and reliable synthesis of 2,3-fused indolines bearing a quaternary carbon. Two C-C bonds can be successively constructed through a tandem sequence involving base-promoted S<sub>N</sub>Ar and aldol condensation. This protocol is highlighted by transition metal-free conditions, high efficiency, and simple operation.
Authors
- Feng‐Cheng Jia (ORCID: https://orcid.org/0000-0002-1290-3018)
- Qun Cai (ORCID: https://orcid.org/0000-0002-7853-9570)
- Zhiping Zheng (ORCID: https://orcid.org/0000-0002-9818-8173)
- Shuang‐Xi Gu (ORCID: https://orcid.org/0000-0003-0159-4616)
- Ziyuan Liu (ORCID: https://orcid.org/0000-0003-2203-612X)
- Ziyi Yuan (ORCID: https://orcid.org/0000-0002-4854-4926)
- Kai-Heng Yu
Institutions
- Green Chemistry (PL)
- Wuhan University of Science and Technology (CN)
- Wuhan Institute of Technology (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-28
- DOI
- https://doi.org/10.1021/acs.joc.5c00301
- Citations
- 1
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Wuhan Institute of Technology
- Hubei Key Laboratory of Novel Reactor and Green Chemistry Technology