ArticleTetrahedron letters2015
S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.
Article in Tetrahedron letters, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Ynamide Coupling Reagents: Origin and Advances.Accounts of chemical research · 2024Article
- 1,3-Butadiynamides the Ethynylogous Ynamides: Synthesis, Properties and Applications in Heterocyclic Chemistry.Molecules (Basel, Switzerland) · 2023Review
- Recent progress in alkynylation with hypervalent iodine reagents.Chemical communications (Cambridge, England) · 2023Review
- Gold-Catalyzed Synthesis of Small Rings.Chemical reviews · 2021Article
- Asymmetric synthesis with ynamides: unique reaction control, chemical diversity and applications.Chemical Society reviews · 2020Article
- Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids.Angewandte Chemie (International ed. in English) · 2019Article
- Preparation and Utility ofMolecules (Basel, Switzerland) · 2019Review
- Synthesis of 3-Amino-1-benzothiophene-1,1-diones by Alkyne Directed Hydroarylation and 1/N→3/C-Sulfonyl Migration.European journal of organic chemistry · 2018Article
- Copper-Promoted Regioselective Intermolecular Diamination of Ynamides: Synthesis of Imidazo[1,2-ACS omega · 2017Article
- Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides.Angewandte Chemie (International ed. in English) · 2016Article
- A Single-Flask Synthesis of α-Alkylidene and α-Benzylidene Lactones from Ethoxyacetylene, Epoxides/Oxetanes, and Carbonyl Compounds.Tetrahedron letters · 2016Article
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2 authors.
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Abstract
Ynamides consist of a polarized triple bond that is directly attached to a nitrogen atom carrying a sulfonyl, an alkoxycarbonyl, an acyl or another electron withdrawing group. The triple bond polarization renders ynamides broadly useful building blocks with synthetic opportunities that go far beyond traditional alkyne chemistry. The versatile reactivity of ynamides in cycloadditions, cycloisomerizations, regioselective additions with various nucleophiles or electrophiles, ring-closing metathesis, and many other reactions has been investigated in detail during the past decades. A common feature of these methods is that the triple bond is consumed and either cleaved or transformed to a new functionality. The wealth of reports on these ynamide reactions is in stark contrast to the dearth of carbon-carbon bond formations that leave the triple bond of terminal ynamides intact. The recent introduction of effective synthetic methods for the preparation of terminal ynamides has set the stage to fully explore the synthetic potential of this intriguing class of compounds. This digest letter summarizes the most effective routes to terminal ynamides and the current state of selective nucleophilic addition, substitution and coupling reactions, including the first examples of asymmetric synthesis.
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