Pd-Catalyzed Deacylative [4 + 1] Annulation of <i>N</i>-Arylimidoyl Chlorides with β-Keto Esters Leading to 2-Fluoroalkyl Indoles

A palladium-catalyzed [4 + 1] annulation of <i>N</i>-arylimidoyl chlorides with β-keto esters has been developed. In the presence of Pd(OAc)<sub>2</sub>, PCy<sub>3</sub>, and K<sub>3</sub>PO<sub>4</sub>, a variety of fluoalkyl-containing <i>N</i>-arylimidoyl chlorides smoothly underwent the cascade C-H imidoylation/deacylative Heck-type reactions to afford biologically important 2-fluoroalkyl indoles in moderate to good yields.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-10
DOI
https://doi.org/10.1021/acs.joc.4c01709
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Pd-Catalyzed Deacylative [4 + 1] Annulation of N-Arylimidoyl Chlorides with β-Keto Esters Leading to 2-Fluoroalkyl Indoles

Zhaolun Wang, Zihan Huang, Hai‐Yong Tu, Xing‐Guo Zhang et al.
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Pd-Catalyzed Deacylative [4 + 1] Annulation of N-Arylimidoyl Chlorides with β-Keto Esters Leading to 2-Fluoroalkyl Indoles

Zhaolun Wang, Zihan Huang, Hai‐Yong Tu, Xing‐Guo Zhang, Zhiyi Zhao, Na Li, Yu-Kai Shao
article en

Abstract

A palladium-catalyzed [4 + 1] annulation of <i>N</i>-arylimidoyl chlorides with β-keto esters has been developed. In the presence of Pd(OAc)<sub>2</sub>, PCy<sub>3</sub>, and K<sub>3</sub>PO<sub>4</sub>, a variety of fluoalkyl-containing <i>N</i>-arylimidoyl chlorides smoothly underwent the cascade C-H imidoylation/deacylative Heck-type reactions to afford biologically important 2-fluoroalkyl indoles in moderate to good yields.

The Journal of Organic ChemistryVol. 89(18)
Wenzhou University (CN)
National Natural Science Foundation of China, Wenzhou University
Openalex Percentile: Top 89%
Fluorine in Organic Chemistry
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