Visible Light-Promoted Reaction of <i>N</i> -Allyl-2-arylindoles with Phosphine Oxides Access to Mono/Diphosphonylated Indolo[2,1- <i>a</i> ] Isoquinolines
An efficient synthesis of phosphonylated indolo[2,1-<i>a</i>]isoquinolines has been developed via visible light-promoted reaction of <i>N</i>-allyl-2-arylindoles with diarylphosphine oxides at room temperature. The reaction afforded monophosphonylated indolo[2,1-<i>a</i>]isoquinolines when indoles had a substituent on the C-3 position. When C-3 unsubstituted <i>N</i>-allyl-2-arylindoles were employed, we obtained diphosphonylated indolo[2,1-<i>a</i>]isoquinolines exclusively. This reaction features advantages such as broad scope of substituents, mild and green conditions, as well as good yields. Moreover, this approach provides a green and the first light-promoted strategy for the synthesis of phosphonylated indolo[2,1-<i>a</i>]isoquinolines derivatives.
Authors
- Hongyun Zhao (ORCID: https://orcid.org/0000-0002-1251-3888)
- Mei Ling Pan (ORCID: https://orcid.org/0000-0002-8979-7305)
- Xingyue Chen
- Guangzhou Zhu
- Junyi Zhu (ORCID: https://orcid.org/0009-0000-7781-0034)
- Yun Liu
- Liangce Rong
Institutions
- Jiangsu Normal University (CN)
- State Key Laboratory of Synthetic Chemistry (CN)
- Green Chemistry (PL)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-01-30
- DOI
- https://doi.org/10.1021/acs.joc.5c02780
- Citations
- 1
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 22.95