Silver-Catalyzed [3 + 2] Cyclization Reaction of α-Azidovinyl Acids with RCF <sub>2</sub> -Imidoyl Sulfoxonium Ylides: Synthesis of Polyfluoroalkyl-Substituted 2 <i>H</i> -Pyrrole Derivatives

A silver-catalyzed [3 + 2] cyclization of α-azidovinyl acids with RCF<sub>2</sub>-imidoyl sulfoxonium ylides has been developed for the first time. This transformation provides an efficient method for constructing polyfluoroalkyl-substituted 2<i>H</i>-pyrroles from readily available precursors with the formation of C-N and C-C bonds in a single step. Further applications, including the synthesis of CF<sub>3</sub>-substituted 1<i>H</i>-pyrrole and <i>N</i>-methyl-4-phenyl-<i>N</i>-(<i>p</i>-tolyl)-2-(trifluoromethyl)-2<i>H</i>-pyrrol-2-amine, demonstrated the immense potential and versatility of this cyclization reaction.

Authors

Institutions

Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-01-22
DOI
https://doi.org/10.1021/acs.joc.5c02888
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00
Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Silver-Catalyzed [3 + 2] Cyclization Reaction of α-Azidovinyl Acids with RCF 2 -Imidoyl Sulfoxonium Ylides: Synthesis of Polyfluoroalkyl-Substituted 2 H -Pyrrole Derivatives

Lixue Su, Hongyu Wang, Ming Yang, Xiaobo Yang et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Silver-Catalyzed [3 + 2] Cyclization Reaction of α-Azidovinyl Acids with RCF 2 -Imidoyl Sulfoxonium Ylides: Synthesis of Polyfluoroalkyl-Substituted 2 H -Pyrrole Derivatives

Lixue Su, Hongyu Wang, Ming Yang, Xiaobo Yang, Xiubin Bu, Yu-Long Zhao, Ruihan Jiang
article en

Abstract

A silver-catalyzed [3 + 2] cyclization of α-azidovinyl acids with RCF<sub>2</sub>-imidoyl sulfoxonium ylides has been developed for the first time. This transformation provides an efficient method for constructing polyfluoroalkyl-substituted 2<i>H</i>-pyrroles from readily available precursors with the formation of C-N and C-C bonds in a single step. Further applications, including the synthesis of CF<sub>3</sub>-substituted 1<i>H</i>-pyrrole and <i>N</i>-methyl-4-phenyl-<i>N</i>-(<i>p</i>-tolyl)-2-(trifluoromethyl)-2<i>H</i>-pyrrol-2-amine, demonstrated the immense potential and versatility of this cyclization reaction.

The Journal of Organic ChemistryVol. 91(5)
Northeast Normal University (CN), Shenyang Normal University (CN), Institute of Catalysis and Petrochemistry (RU), Laboratoire de Synthèse Organique (FR)
Clean water and sanitation
Openalex Percentile: Top 82%
Catalytic C–H Functionalization Methods
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.