Radical-Initiated Dearomative Annulation of Tryptamine-Derived Isocyanides: Selective Synthesis of CF<sub>3</sub>-Substituted β-Aza-spiroindolines and β-Carbolines

A mild approach for synthesizing CF<sub>3</sub>-substituted β-aza-spiroindolines and β-carbolines from tryptamine-derived isocyanides via site-selective radical annulations has been reported. The crucial role of C2 substituents in the selective annulation process has been clarified. The approach shows good generality and practical applicability, highlighting its effectiveness and versatility.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-10-22
DOI
https://doi.org/10.1021/acs.joc.4c02302
Citations
4
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.00

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article

Radical-Initiated Dearomative Annulation of Tryptamine-Derived Isocyanides: Selective Synthesis of CF3-Substituted β-Aza-spiroindolines and β-Carbolines

Xiaoping Xu, Luo-Rong Yuan, You Zi, Shun‐Jun Ji
4 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
1.00
article

Radical-Initiated Dearomative Annulation of Tryptamine-Derived Isocyanides: Selective Synthesis of CF3-Substituted β-Aza-spiroindolines and β-Carbolines

Xiaoping Xu, Luo-Rong Yuan, You Zi, Shun‐Jun Ji
article en
4 citations

Abstract

A mild approach for synthesizing CF<sub>3</sub>-substituted β-aza-spiroindolines and β-carbolines from tryptamine-derived isocyanides via site-selective radical annulations has been reported. The crucial role of C2 substituents in the selective annulation process has been clarified. The approach shows good generality and practical applicability, highlighting its effectiveness and versatility.

The Journal of Organic ChemistryVol. 89(21)
Nantong University (CN), Soochow University (CN), Laboratoire de Synthèse Organique (FR)
National Natural Science Foundation of China, Natural Science Foundation of Jiangsu Province, Priority Academic Program Development of Jiangsu Higher Education Institutions
Openalex Percentile: Top 26%
Catalytic C–H Functionalization Methods
1.00
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