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Journal ArticleDOI

Copper-Catalyzed Rearrangement of (Z)-Propynal Hydrazones via N−N Bond Cleavage

Itaru Nakamura, +3 more
- 18 Aug 2010 - 
- Vol. 12, Iss: 18, pp 4198-4200
TLDR
Propynal hydrazones are successfully converted to the corresponding 3-aminoacrylonitriles in the presence of copper catalysts in good to high yields through C-N bond formation and subsequent β-elimination involving cleavage of N-N and C-H bonds.
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This article is published in Organic Letters.The article was published on 2010-08-18. It has received 18 citations till now. The article focuses on the topics: Propynal & Bond cleavage.

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Citations
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Effects of base strength on the copper-catalyzed cycloisomerization of propargylic acetates to form indolizines: A DFT study

TL;DR: In this article, the base strength is the primary factor that controls the catalytic capability of cocatalysts CH3CN, Propargylic acetates (1a) and Et3N.
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Theoretical investigation on the mechanism of Cu(II)-catalyzed synthesis of 4-quinolones: effects of additives HOTf vs. HOTs

TL;DR: In this article, a computational study with the B3LYP density functional is carried out to explore the effects of additives (HOTf vs. HOTs) on the Cu(OTf)2-catalyzed synthesis of 4-quinolones.
Journal ArticleDOI

Chemoselective Hydroalumination of 1-Aza-but-1-en-3-ynes (C-Iminoalkynes): Formation of Propargylamines by Imine Reduction and of 5-Aluminazoles and 1-Aza-butadienes by Anti-Michael Attack

TL;DR: In this article, it was shown that the observed chemoselectivity is only compatible with a dimeric nature of the hydroaluminating agent, and that the imine reduction corresponds to the kinetically controlled pathway, whereas the triple bond reduction leads to the thermodynamically much more stabl...
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Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones.

TL;DR: In this paper , the Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles involving the cleavage of an N-N bond is reported.
Journal ArticleDOI

Copper‐Catalyzed Synthesis of Alkynyl Hydrazones from Alkynes and Hydrazonyl Chlorides

TL;DR: A novel ligand-free synthesis of alkynyl hydrazones via coupling reaction of hydrazonyl chlorides and terminal alkynes, catalyzed by CuI led to excellent yields.
References
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Journal ArticleDOI

Gold-Catalyzed Organic Reactions

TL;DR: Important vinylgold intermediates, the transmetalation from gold to other transition metals, the development of new ligands for gold catalysis, and significant contributions from computational chemistry are other crucial points for the field highlighted here.
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Catalytic Carbophilic Activation: Catalysis by Platinum and Gold π Acids

TL;DR: The ability of platinum and gold catalysts to effect powerful atom-economic transformations has led to a marked increase in their utilization and the application of platinum- and gold-catalyzed transformations in natural product synthesis is discussed.
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Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective.

TL;DR: The proposed involvement of cyclopropyl metal carbenes of type 4 in the electrophilic activation of enynes by transition metals was first substantiated in reactions catalyzed by Pd(II), in which the initially formed cycloprostyl palladiumCarbenes undergo [4 + 2] cycloaddition with the double bond of the conjugate enyne.
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Gold-catalyzed organic transformations.

TL;DR: Thanks to gold-based catalysts, various organic transformations have been accessible under facile conditions with both high yields and chemoselectivity.
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Relativistic effects in homogeneous gold catalysis

TL;DR: This Review draws on experimental and computational data to present the current understanding of homogeneous gold catalysis, focusing on previously unexplored reactivity and its application to the development of new methodology.
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