Gold-Catalyzed Transformation of Ynamides
Shashank Shandilya1, Manash Protim Gogoi1, Shubham Dutta1
1School of Chemistry, University of Hyderabad, 500046, Hyderabad, India.
Chemical Record (New York, N.Y.)
|August 25, 2021
Summary
This review explores gold-catalyzed reactions of ynamides, highlighting their use in synthesizing novel N-bearing heterocycles. It details ynamide transformations involving nitrogen-transfer, oxygen-transfer, and carbon nucleophiles, offering mechanistic insights.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Ynamides possess unique electronic properties, with nitrogen lone pair polarization extending to the triple bond.
- They are valuable synthons for creating novel nitrogen-containing heterocyclic compounds.
- Recent reviews have covered ynamide versatility in umpolung, radical, and asymmetric synthesis.
Purpose of the Study:
- To provide a comprehensive overview of gold-catalyzed transformations involving ynamides.
- To elucidate the reactivity of ynamides with various transfer reagents (N, O, C) under gold catalysis.
- To briefly discuss the scope and mechanistic pathways of these reactions.
Main Methods:
- Review of existing literature on gold-catalyzed ynamide reactions.
- Categorization of reactions based on the type of transfer reagent: nitrogen, oxygen, and carbon nucleophiles.
- Analysis of reported reaction scopes and mechanistic proposals.
Main Results:
- Detailed examination of ynamide reactivity with nitrogen-transfer reagents (azides, nitrogen ylides, isoxazoles, anthranils).
- Exploration of ynamide transformations with oxygen atom-transfer reagents (nitrones, sulfoxides, pyridine N-oxides).
- Uncovering of ynamide reactions involving carbon nucleophiles under gold catalysis.
Conclusions:
- Gold catalysis significantly expands the synthetic utility of ynamides.
- Ynamides exhibit diverse reactivity patterns with various electrophilic and nucleophilic partners.
- This review consolidates key gold-catalyzed ynamide reactions, aiding future synthetic design.
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