Visible-Light-Induced Multifunctionalization Reaction of <i>o</i>-Alkenyl Aromatic Isocyanides, Sulfur Ylide, and Fluorinated Alcohols: Direct Synthesis of 3-Fluoroalkyl-Substituted Indoles

A visible-light-induced multicomponent tandem cyclization of <i>o</i>-alkenyl aromatic isocyanides with fluorinated alcohols and sulfur ylides as carbon radical precursors was developed for the first time. This reaction provides an efficient method for the construction of 3-fluoroalkyl-substituted indoles from readily available acyclic starting materials with the formation of two C-O bonds and two C-C bonds in a single step. Further applications, including synthesis of 2-(1<i>H</i>-indol-2-yl)-1,4-diphenylbutane-1,4-diol,2-(thiophen-3-yl/1<i>H</i>-pyrrol-3-yl)-1<i>H</i>-indoles and 9<i>H</i>-carbazole, demonstrated the tremendous potential of the multicomponent reaction.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-09-20
DOI
https://doi.org/10.1021/acs.joc.5c01645
Citations
6
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
5.62
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article

Visible-Light-Induced Multifunctionalization Reaction of o-Alkenyl Aromatic Isocyanides, Sulfur Ylide, and Fluorinated Alcohols: Direct Synthesis of 3-Fluoroalkyl-Substituted Indoles

Xue‐Cen Xu, Yuxuan Meng, Yue Gong, Yu‐Long Zhao et al.
6 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
5.62
article

Visible-Light-Induced Multifunctionalization Reaction of o-Alkenyl Aromatic Isocyanides, Sulfur Ylide, and Fluorinated Alcohols: Direct Synthesis of 3-Fluoroalkyl-Substituted Indoles

Xue‐Cen Xu, Yuxuan Meng, Yue Gong, Yu‐Long Zhao, Jie Wang
article en
6 citations

Abstract

A visible-light-induced multicomponent tandem cyclization of <i>o</i>-alkenyl aromatic isocyanides with fluorinated alcohols and sulfur ylides as carbon radical precursors was developed for the first time. This reaction provides an efficient method for the construction of 3-fluoroalkyl-substituted indoles from readily available acyclic starting materials with the formation of two C-O bonds and two C-C bonds in a single step. Further applications, including synthesis of 2-(1<i>H</i>-indol-2-yl)-1,4-diphenylbutane-1,4-diol,2-(thiophen-3-yl/1<i>H</i>-pyrrol-3-yl)-1<i>H</i>-indoles and 9<i>H</i>-carbazole, demonstrated the tremendous potential of the multicomponent reaction.

The Journal of Organic ChemistryVol. 90(39)
Northeast Normal University (CN), Laboratoire de Synthèse Organique (FR)
Openalex Percentile: Top 4%
Radical Photochemical Reactions
5.62
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Visible-Light-Induced Multifunctionalization Reaction of <i>o</i>-Alkenyl Aromatic Isocyanides, Sulfur Ylide, and Fluorinated Alcohols: Direct Synthesis of 3-Fluoroalkyl-Substituted Indoles — Xue‐Cen Xu, Yuxuan Meng, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS