NIS-Promoted Cascade Electrophilic Spirocyclization of Aryl Alkyne-Tethered Indoles to Construct Iodinated Spiroindolenines

A highly efficient and general cascade electrophilic spirocyclization reaction of aryl alkyne-tethered indoles with <i>N</i>-iodosuccinimide (NIS) has been developed under mild conditions. A diverse range of iodinated spiroindolenines were successfully constructed in moderate to excellent yields without relying on metal reagents, strong oxidants, photochemical activation, or electrochemical assistance. Moreover, this protocol demonstrates good functional group tolerance, mild reaction conditions, feasibility for gram-scale synthesis, and versatile practical applications.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-18
DOI
https://doi.org/10.1021/acs.joc.5c02567
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

NIS-Promoted Cascade Electrophilic Spirocyclization of Aryl Alkyne-Tethered Indoles to Construct Iodinated Spiroindolenines

Qiang Xiao, Qiu‐Quan Pan, Mu‐Jia Luo, Ruchun Yang et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

NIS-Promoted Cascade Electrophilic Spirocyclization of Aryl Alkyne-Tethered Indoles to Construct Iodinated Spiroindolenines

Qiang Xiao, Qiu‐Quan Pan, Mu‐Jia Luo, Ruchun Yang, Meng Liang, Xingyue Wang, Xian‐Rong Song, Jiang Bai, Fengyan Jin
article en

Abstract

A highly efficient and general cascade electrophilic spirocyclization reaction of aryl alkyne-tethered indoles with <i>N</i>-iodosuccinimide (NIS) has been developed under mild conditions. A diverse range of iodinated spiroindolenines were successfully constructed in moderate to excellent yields without relying on metal reagents, strong oxidants, photochemical activation, or electrochemical assistance. Moreover, this protocol demonstrates good functional group tolerance, mild reaction conditions, feasibility for gram-scale synthesis, and versatile practical applications.

The Journal of Organic ChemistryVol. 91(1)
Jiangxi Science and Technology Normal University (CN)
Openalex Percentile: Top 69%
Catalytic C–H Functionalization Methods
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