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.

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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
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article

Visible Light-Promoted Reaction of N -Allyl-2-arylindoles with Phosphine Oxides Access to Mono/Diphosphonylated Indolo[2,1- a ] Isoquinolines

Hongyun Zhao, Mei Ling Pan, Xingyue Chen, Guangzhou Zhu et al.
1 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
22.95
article

Visible Light-Promoted Reaction of N -Allyl-2-arylindoles with Phosphine Oxides Access to Mono/Diphosphonylated Indolo[2,1- a ] Isoquinolines

Hongyun Zhao, Mei Ling Pan, Xingyue Chen, Guangzhou Zhu, Junyi Zhu, Yun Liu, Liangce Rong
article en
1 citations

Abstract

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.

The Journal of Organic ChemistryVol. 91(6)
Jiangsu Normal University (CN), State Key Laboratory of Synthetic Chemistry (CN), Green Chemistry (PL)
Openalex Percentile: Top 1%
Radical Photochemical Reactions
22.95
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