Direct C4 Halogenation of Isoquinolines via a Boc<sub>2</sub>O-Mediated Dearomatization Strategy
A cost-effective method for directly halogenating isoquinolines at the C4 position has been developed through a one-pot sequence involving Boc<sub>2</sub>O-mediated dearomatization, electrophilic halogenation (X = Cl, Br, I), and acid-promoted rearomatization. This reaction exhibited high C4 site selectivity, efficiently affording 4-halogenated isoquinolines, and demonstrated good functional group tolerance at C5-C8. In addition, the C-X bond-containing products could serve as versatile synthetic intermediates for further modification of isoquinolines, including Suzuki coupling, Sonogashira coupling, and Stille coupling.
Authors
- Jiangtao Cai (ORCID: https://orcid.org/0000-0001-5031-265X)
- Jinming Zhou (ORCID: https://orcid.org/0000-0003-1610-5061)
- Byeung Mun Song
- Xiaoli Han (ORCID: https://orcid.org/0000-0002-4297-8934)
- Dazhong Yuan
- Fengjiao Xiang
Institutions
- Zhejiang Normal University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-16
- DOI
- https://doi.org/10.1021/acs.joc.5c00535
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94