Synthesis of Acyclic Quaternary α-CF <sub>3</sub> -β-Oxo Carbonyls via Nucleophilic Substitution Induced by Single-Electron Transfer

The development of efficient methods for the formation of quaternary centers in organic compounds has been a constant challenge in synthetic chemistry. Quaternary β-oxo esters are fundamental structures in the synthesis of natural products, pharmaceutical compounds, and other bioactive molecules. In this work, a direct and versatile approach to quaternary noncyclic β-oxo esters is reported using trifluoromethyl thianthrenium salt as highly reactive and selective reagent under mild conditions. Mechanistic investigations supported the operation via single-electron transfer-induced nucleophilic substitution.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-11-06
DOI
https://doi.org/10.1021/acs.joc.5c01559
Citations
1
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.79
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article

Synthesis of Acyclic Quaternary α-CF 3 -β-Oxo Carbonyls via Nucleophilic Substitution Induced by Single-Electron Transfer

Albert Granados, Carolina Gimbert‐Suriñach, Xiangyu Tan, Adelina Vallribera et al.
1 citations
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
0.79
article

Synthesis of Acyclic Quaternary α-CF 3 -β-Oxo Carbonyls via Nucleophilic Substitution Induced by Single-Electron Transfer

Albert Granados, Carolina Gimbert‐Suriñach, Xiangyu Tan, Adelina Vallribera, Pau Sarró, Elı́es Molins, Roser Pleixats
article en
1 citations

Abstract

The development of efficient methods for the formation of quaternary centers in organic compounds has been a constant challenge in synthetic chemistry. Quaternary β-oxo esters are fundamental structures in the synthesis of natural products, pharmaceutical compounds, and other bioactive molecules. In this work, a direct and versatile approach to quaternary noncyclic β-oxo esters is reported using trifluoromethyl thianthrenium salt as highly reactive and selective reagent under mild conditions. Mechanistic investigations supported the operation via single-electron transfer-induced nucleophilic substitution.

The Journal of Organic ChemistryVol. 90(45)
Universitat Autònoma de Barcelona (ES), Institut de Ciència de Materials de Barcelona (ES), ORFEO-CINQA Research Network (ES)
Openalex Percentile: Top 22%
Fluorine in Organic Chemistry
0.79
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Synthesis of Acyclic Quaternary α-CF <sub>3</sub> -β-Oxo Carbonyls via Nucleophilic Substitution Induced by Single-Electron Transfer — Albert Granados, Carolina Gimbert‐Suriñach, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS