General Amination Reactions for the Synthesis of Ynamides

Abstract

The development of general syntheses of ynamides and related compounds based on various amination strategies are described in this short review. Reactions are classified according to the type of amination used and comparisons are made between all strategies to provide a comprehensive overview and to emphasize the advantages and limitations of each method.

1 Introduction: The ABC of Ynamides

2 Synthesis of Ynamides at the Dawn of the 21st Century: Elimination and Isomerization

3 Synthesis of Ynamides by Amination of/with Hypervalent Iodonium Salts

4 The Emergence of General Syntheses of Ynamides: Copper-Mediated Amination of Bromoalkynes, gem-Dibromo­alkenes, and Alkynyl(triaryl)bismuthonium Tetrafluoro­borates

5 Alternative Practical and Mild Syntheses of Ynamides: Copper­-Catalyzed Oxidative Amination of Alkynes, Potassium­ Alkynyltrifluoroborates, and Propiolic Acids

6 ‘Click’ Oxidative Amination of Copper Acetylides: A Practical Entry to Ynamides under Mild Conditions

7 Synthesis of Ynehydrazides by Electrophilic Amination of Lithium Acetylides with Diazodicarboxylates

8 Conclusions and Outlook: Ynamides Synthesis, Where Now?

Key words

ynamines - ynamides - N-alkynyl heterocycles - amination - copper catalysis - alkynes

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