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AbstractNitrogen heterocycles are some of the most important and sought-after structural motifs in synthetic chemistry. General methods that can be applied towards a structurally diverse range of different scaffolds are rare. This Focus Review discusses an emerging area with the field of π-acid catalysis based on the activation of carbon-carbon triple bonds in conjunction with nucleophilic nitrenoids. The resulting approach provides ready access into α-imino metal carbene reactivity patterns that can be employed in a number of quenching processes to realize a variety of powerful new transformations. The resulting methods are characterized by high efficiency, simple and straightforward reaction set ups, mild conditions, and excellent functional group tolerance. In this Focus Review the different nucleophilic nitrenoid types are explored showing how they can be used across a range of (poly)cyclization and formal cycloaddition processes to provide an alternative and direct disconnection pathway in the generation of N-heterocyclic motifs.Do you want to read the rest of this article?
CitationsCitations6ReferencesReferences142ABSTRACT: A three-component gold(I)-catalyzed synthesis of 2-imidazoyl-1-pyrazolylbenzenes from 1-propargyl-1H-benzotriazoles is described here. Initially the benzotriazole derivative suffers an intramolecular 5-endo-dig cyclization to form a triazapentalene. This dipolar compound is able to perform an intermolecular and regioselective attack to a gold-activated alkyne. After triazole breakage, the pyrazole ring and an α-imino gold carbene complex are formed. Finally, the iminocarbene is captured by a nitrile to form an imidazole ring.Article · Mar 2016 ABSTRACT: A gold-catalyzed regioselective [3+2] cycloaddition of ynamides with 1,4,2-dioxazoles has been developed, which offers a novel approach to highly functionalized oxazoles under mild reaction conditions. 1,4,2-Dioxazole was found to act as an efficient N-acyl nitrene equivalent to trigger a facile generation of a-imino gold-carbene intermediate through the elimination of a ketone.Article · Apr 2016 ABSTRACT: The recently developed nitrene transfer reaction onto gold-activated alkynes provides a route to safe and accessible synthons of α-diazo imides. This reaction is rather unique in that it requires AuI
however, this promiscuous metal is only used to activate the alkyne moiety. After such activation is obtained, the nitrene-transfer process occurs through an outer-sphere mechanism, in which the metal acts only as a spectator. Density functional theory was applied to elucidate this peculiar reaction and to provide a mechanistic explanation for the experimentally observed isomers at the double bond and imine sites.Article · Jun 2016 +1 more author ...ArticleSeptember 2016 · Journal of the American Chemical Society · Impact Factor: 12.11+1 more author…ArticleSeptember 2016 · Organic Letters · Impact Factor: 6.36ArticleSeptember 2016 · The Journal of Organic Chemistry · Impact Factor: 4.72ArticleSeptember 2016 · The Journal of Organic Chemistry · Impact Factor: 4.72Data provided are for informational purposes only. Although carefully collected, accuracy cannot be guaranteed. Publisher conditions are provided by RoMEO. Differing provisions from the publisher's actual policy or licence agreement may be applicable.This publication is from a journal that may support self archiving.Last Updated: 02 Sep 16
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多组分反应合成杂环Topics in Heterocyclic Chemistry, Vol 25：Synthesis of Heterocyc.
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