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Synthesis 2013; 45(1): 17-26
DOI: 10.1055/s-0032-1317880
DOI: 10.1055/s-0032-1317880
short review
General Amination Reactions for the Synthesis of Ynamides
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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For a correction, see:
For general references on the chemistry of ynamines, see:
For recent reviews on the chemistry of ynamides, see:
For selected key references on the development of new reactions from ynamides over the last five years, see:
For the use of ynamides in natural product synthesis, see:
For a review on the chemistry of hypervalent alkynyliodonium salts, see:
For a review on electrophilic alkynylation, see:
Representative examples with metalated sulfonamides:
Also see refs. 6k and 14d. Representative examples with metalated amides:
Also see refs. 7b and 15a. Representative example with metalated carbamates:
Representative examples of intramolecular versions:
Representative examples with metalated N-heterocycles:
For reviews on copper catalysis, see:
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