Synthesis 2013; 45(1): 17-26
DOI: 10.1055/s-0032-1317880
short review
© Georg Thieme Verlag Stuttgart · New York

General Amination Reactions for the Synthesis of Ynamides

Gwilherm Evano*
a  Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université Libre de Bruxelles, Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium   Fax: +32(2)6502798   Email: [email protected]
,
Kévin Jouvin
b  Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France
,
Alexis Coste
b  Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France
› Author Affiliations
Further Information

Publication History

Received: 30 October 2012

Accepted after revision: 22 November 2012

Publication Date:
03 December 2012 (online)


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?

 
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