C-H activation and functionalization is quite promising in recent days as the strategy offers a go-to general method for different bond formations and hence grants synthetic versatility. At the same time, imidazopyridine, a fused bicycle of imidazole moiety with pyridine ring, has a profound impact due to its ubiquitous and prodigious application in medicinal as well as material chemistry. The presence of N-1 atom in 2-arylImidazo[1,2-a]pyridine facilitates the coordination with metal catalysts leading to the formation of ortho-substituted products. This review summarizes all the articles on ortho C-H functionalization of 2-arylImidazo[1,2-a]pyridines published till August 2021.
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Cp*Co(III)-catalyzed -alkylation/alkenylation of anilides.
Org Biomol Chem
January 2025
College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, 473061, P. R. China.
A highly practical and efficient Cp*Co(III)-catalyzed C-H alkylation/alkenylation reaction of anilides with maleimides and acrylates was developed, during which a weakly coordinating amide carbonyl group functioned as the directing group. This approach features high efficiency, good functional group tolerance, and broad substrate scope, and a variety of 3-substituted succinimides and -alkenylated anilides were synthesized in moderate to excellent yields. Furthermore, the reaction is highly selective, affording mono--alkylated/alkenylated products only.
View Article and Find Full Text PDFRu(II)-Catalyzed -Vinylation of Benzoic Acids in Water.
J Org Chem
January 2025
Department of Chemistry, Malaviya National Institute of Technology Jaipur, Jaipur 302017, Rajasthan, India.
Article Synopsis
- A new method for the oxidative C-H alkenylation of benzoic acid using [Ru(η-CH)Cl] catalyst has been developed, operating efficiently in water at mild temperatures (60 °C).
- The reaction shows regioselectivity, producing mono-olefinated products when using activated alkenes like acrylates, while both mono and diolefinated products emerge from unactivated alkenes such as styrene.
- A novel five-membered cyclic compound was formed from vinylferrocene as a coupling partner, indicating a unique reactivity profile compared to other alkenes.
Synthesis of Rigid Stepladder Polymers Scandium-Catalyzed Polyspiroannulation of Quinoline with Alkyne.
J Am Chem Soc
January 2025
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
Article Synopsis
- The study focuses on the development of a new type of rigid, three-dimensional polymers known as stepladder polymers, utilizing spirodihydroquinoline structures.
- These polymers are created through a reaction facilitated by a scandium catalyst that activates specific chemical bonds, allowing for the formation of complex structures from quinoline and alkyne compounds.
- The resulting polymers have increased thermal stability and porosity after undergoing a treatment that adds a methyl group to their nitrogen-containing functional groups.
Oxidative coupling of N-nitrosoanilines with substituted allyl alcohols under rhodium (III) catalysis.
Front Chem
December 2024
Department of Chemistry, University of Lucknow, Lucknow, India.
Rhodium(III) catalysis has been used for C-H activation of -nitrosoanilines with substituted allyl alcohols. This method provides an efficient synthesis of the functional -nitroso β-aryl aldehydes and ketones with low catalyst loading, high functional group tolerance, and superior reactivity of allyl alcohols toward -nitrosoanilines. We demonstrated that reaction also proceeds through the one-pot synthesis of -nitrosoaniline, followed by subsequent, C-H activation.
View Article and Find Full Text PDFPhosphite mediated molecular editing switch to -C-H alkylation of isoquinolines: emergence of a distinct photochemical [1,3] N to C rearrangement.
Chem Sci
January 2025
Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL) Pune 411 008 India
The isoquinoline core is present in one of the largest subsets of bioactive natural products. The multifunctional isoquinoline core exerts diverse bioactivity, resulting in the development of numerous isoquinoline-based drugs and molecules that are currently under clinical trials. We developed a new approach for phosphite-mediated [1,2] alkyl migration for an overall -C-H alkylation -alkylation of isoquinoline.
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