In the last decade, aryldiazonium salts have attracted interest as coupling partners in cross-coupling reactions mediated by gold. Initially, the presence of a photocatalyst and a light source was needed to achieve gold oxidation with these electrophiles. However, recently, it has been shown that in some instances just heating, light irradiation, or the addition of certain bases and/or nucleophiles is enough. In this review, the transformations developed so far using aryldiazonium salts as electrophiles are summarized with special emphasis on mechanistic studies. The information gained by different authors, indicates that the specific steps of gold oxidation with aryldiazonium salts depends upon the activation mode of the diazonium salt.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.202000884 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of Aryl Alkyl Thioethers via a Copper-Catalyzed Three-Component Reaction with DABSO, Aryldiazonium Salts, and Alkyl Bromides.
J Org Chem
October 2024
Department of Chemistry, Chonnam National University, Gwangju 61186, Republic of Korea.
We developed a method for synthesizing aryl alkyl thioether compounds via a three-component reaction involving aryldiazonium salts, 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide), and alkyl bromides.
View Article and Find Full Text PDFThe Positional Effect of an Immobilized Re Tricarbonyl Catalyst for CO Reduction.
ACS Appl Mater Interfaces
September 2024
Department of Chemistry, University of Southern California, California, Los Angeles 90089, United States.
The storage of renewable energy through the conversion of CO to CO provides a viable solution for the intermittent nature of these energy sources. The immobilization of rhenium(I) tricarbonyl molecular complexes is presented through the reductive coupling of bis(diazonium) aryl substituents. The heterogenized complex was characterized through ultra-visible, attenuated total reflectance, infrared reflection absorption spectroscopy, and X-ray photoelectron spectroscopy to probe the electronic structure of the immobilized complex.
View Article and Find Full Text PDFRapid synthesis of azoindolizine derivatives via aryldiazonium salts.
Turk J Chem
March 2024
Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkiye.
A practical, rapid, and efficient method for the synthesis of azoindolizine derivatives via aryldiazonium salts with excellent yields was reported. Firstly, the corresponding aniline derivatives were synthesized via a simple and rapid method. Then, the optimal reaction conditions were investigated using a variety of protic and aprotic solvents that demonstrating the robustness of the approach.
View Article and Find Full Text PDFStraightforward Access to Isoindoles and 1,2-Dihydrophthalazines Enabled by a Gold-Catalyzed Three-Component Reaction.
J Org Chem
July 2024
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, Ciudad de México 04510, México.
We describe herein a gold-catalyzed three-component reaction of -alkynylbenzaldehydes, aryldiazonium salts, and trimethoxybenzene. This process enables the one-pot formation of valuable isoindoles and 1,2-dihydrophathalazines. The regioselectivity of the reaction is dictated by the nature of the aryldiazonium salt.
View Article and Find Full Text PDFDivergent Synthesis of 2-Chromonyl-3-hydrazono-chromones and 2-Alkoxy-3-hydrazono-chromones through Switchable Annulation Reactions of -Hydroxyphenylenaminones with Aryldiazonium Salts.
Org Lett
June 2024
Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, China.
An unprecedented selective chromone annulation reaction controlled by solvent for the divergent synthesis of two types of 2,3-disubstituted chromone skeletons has been developed. A variety of 2-chromonyl-3-hydrazono-chromones and 2-alkoxy-3-hydrazono-chromones were constructed efficiently from readily available -hydroxyphenylenaminones (-HPEs) and aryldiazonium salts at room temperature. This strategy is highly chemoselective and features mild reaction conditions, broad substrate scope, broad functional group tolerance, easy gram-scale preparation, and simple filtration to obtain the pure products without tedious column chromatography.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!