Journal ArticleDOI
A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides.
Michael O. Frederick,Jason A. Mulder,Michael R. Tracey,Richard P. Hsung,Jian Huang,Kimberly C. M. Kurtz,Lichun Shen,Christopher J. Douglas +7 more
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A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides, which should have a significant impact on the future development of synthetic methodologies employing ynamide.Abstract:
A copper-catalyzed new C−N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing ynamides.read more
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Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.
TL;DR: Using R-Hydroxy Stannanes as a Model for a Methylenation Reaction and Conclusions and Future Prospects are presented.
Journal ArticleDOI
Copper in cross-coupling reactions: The post-Ullmann chemistry
TL;DR: A number of methods using various copper complexes and salts to carry out cross-coupling reactions leading to the formation of C heteroatom (C N, C O, C S, C P, C Se), C C, and C metal bonds have been proposed as discussed by the authors.
Journal ArticleDOI
Ynamides: A Modern Functional Group For The New Millennium
Kyle A. DeKorver,Hongyan Li,Andrew G. Lohse,Ryuji Hayashi,Zhenjie Lu,Yu Zhang,Richard P. Hsung +6 more
TL;DR: Ynamines are very sensitive toward hydrolysis, as protonation of the electron-rich alkynyl motif affords reactive keteniminium intermediates, which upon trapping with water leads to simple amides in a rather expensive manner (Scheme i), which has caused much difficulty in the experimental preparation and general handling of ynamines, and more detrimentally, rendered ynamine chemistry inaccessible.
Journal ArticleDOI
Ynamides: versatile tools in organic synthesis.
TL;DR: This Review highlights major developments in nitrogen-substituted alkynes and offers unique and multiple opportunities for the inclusion of nitrogen-based functionalities into organic molecules.
Journal ArticleDOI
Diamine ligands in copper -catalyzed reactions
TL;DR: The use of diamine-based ligands has been important in these advances and in this review we discuss these systems, including the choice of reaction conditions and applications in the synthesis of pharmaceuticals, natural products and designed materials as mentioned in this paper.
References
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Journal ArticleDOI
Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism.
TL;DR: Oxidative addition and reductive elimination are the central steps in new palladium-catalyzed chemistry that forms C-N and C-O bonds in arylamines and ethers.
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A general and efficient copper catalyst for the amidation of aryl halides.
TL;DR: Catalyst systems based on N,N'-dimethylethylenediamine or trans-N,N'dimethyl-1,2-cyclohexanediamine were found to be the most active even though several other 1, 2-diamine ligands could be used in the easiest cases.
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Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates
TL;DR: These ligands are effective for almost all substrate combinations that have been previously reported with various other ligands, and they represent the most generally effective catalyst system reported to date.