A robust, selective, and highly efficient method for the preparation of 1,3,4-triaryl 1,2,3-triazolium salts has been developed. It features arylation of a click triazole with a diaryliodonium salt in the presence of a copper catalyst under neat conditions. The presence of pyridine functionality is tolerated, enabling the first access to key precursors of pyridyl-mesoionic carbene ligands. The method has been integrated into a one-pot protocol with terminal alkyne, sodium azide, and diaryliodonium salt as starting compounds.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.9b02197 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Solar Light-Induced Synthesis of Biologically Active Compounds.
Curr Top Med Chem
September 2024
Department of Mathematics and Natural Sciences, College of Sciences and Human Studies, Deanship of Research, Prince Mohammad Bin Fahd University, Al Khobar 31952, Kingdom of Saudi Arabia.
Over the past few years, photocatalytic methods have shown great promise as low-cost, environmentally friendly, and sustainable technologies. During the development of photochemistry, a variety of sources of light were used, including sunlight, compact fluorescent lamps, lasers, and even light-emitting diodes. As a part of preparing diverse organic compounds, the photochemical approach was used, for instance, to form rings, arylated compounds, cycloaddition, functionalized compounds, dehalogenated compounds, oxidized compounds, reduced compounds, isomers, and sensitized compounds.
View Article and Find Full Text PDFDesign and synthesis of 1,2-dihydroquinoline/chromene fused sugar triazole frameworks by copper-catalyzed one-pot click and intramolecular arylation reactions.
Org Biomol Chem
August 2024
Organic Synthesis Laboratory, Department of Chemistry, Ravenshaw University, Cuttack-753003, Odisha, India.
Expedient copper-catalyzed one-pot click and intramolecular arylation reactions have been developed for the synthesis of 1,2-dihydroquinoline/chromene-fused triazoles with varying sugar functionalities. It has been observed that the additive TMEDA greatly facilitates this copper-catalyzed cyclization. This reaction involves two mechanistically distinct reactions an atom-economical click reaction and a direct arylation of a sugar triazole.
View Article and Find Full Text PDF"On-Water" accelerated dearomative cycloaddition via aquaphotocatalysis.
Nat Commun
May 2024
Department of Chemistry, Sungkyunkwan University, Suwon, 16419, Republic of Korea.
Sulfur(VI) fluoride exchange (SuFEx) has emerged as an innovative click chemistry to harness the pivotal connectivity of sulfonyl fluorides. Synthesizing such alkylated S(VI) molecules through a straightforward process is of paramount importance, and their water-compatibility opens the door to a plethora of applications in biorelevant and materials chemistry. Prior aquatic endeavors have primarily focused on delivering catalysts involving ionic mechanisms, studies regarding visible-light photocatalytic transformation are unprecedented.
View Article and Find Full Text PDFHarnessing Sulfur(VI) Fluoride Exchange Click Chemistry and Photocatalysis for Deaminative Benzylic Arylation.
ACS Catal
June 2023
Department of Chemistry, Texas A&M University, College Station, Texas, 77843, United States.
While among the most common functional handles present in organic molecules, amines are a widely underutilized linchpin for C-C bond formation. To facilitate C-N bond cleavage, large activating groups are typically used but result in the generation of stoichiometric amounts of organic waste. Herein, we report an atom-economic activation of benzylic primary amines relying on the Sulfur(VI) Fluoride Exchange (SuFEx) click chemistry and the -Ramberg-Bäcklund reaction.
View Article and Find Full Text PDFTyrosol-Derived Biodegradable Inks with Tunable Properties for 3D Printing.
ACS Biomater Sci Eng
September 2021
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.
Three-dimensional (3D) printing has emerged as a valuable tool in medicine over the past few decades. With a growing number of applications using this advanced processing technique, new polymer libraries with varied properties are required. Herein, we investigate tyrosol-based poly(ester-arylate)s as biodegradable inks in fused deposition modeling (FDM).
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!