ChemInform Abstract: Pyridine and Related Ligands in Transition Metal Homogeneous Catalysis

Zafar, Muhammad Nadeem; Atif, A. H.; Nazar, Muhammad Faizan; Sumrra, Sajjad Hussain; Gul‐E‐Saba, Gul‐E‐Saba; Paracha, Rizwan Nasir

doi:10.1002/chin.201648230

Cited by 5 publications

(6 citation statements)

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“…P yridine is a valuable motif found in a wide range of natural products, 1 biologically active molecules, 2 and functional materials. 3 Along these lines, there is a growing demand for the regioselective introduction of alkyl groups to the privileged pyridine scaffolds. 4 Among synthetic strategies, direct C−H alkylation using readily available alkyl halides has emerged as an increasingly popular approach.…”

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confidence: 99%

Visible-Light-Driven C4-Selective Alkylation of Pyridinium Derivatives with Alkyl Bromides

et al. 2020

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Reported herein is a general strategy for the photochemical cross-coupling between N-amidopyridinium salts and various alkyl bromides under photocatalyst-free conditions, granting facile access to various C4-alkylated pyridines. This approach exploits the intriguing photochemical activity of electron donor–acceptor (EDA) complexes between N-amidopyridinium salts and bromide, which provides a photoactive handle capable of generating silyl radicals and driving the alkylation process. The robustness of this protocol was further demonstrated by the late-stage functionalization of complex compounds under mild and metal-free conditions.

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confidence: 99%

Visible-Light-Driven C4-Selective Alkylation of Pyridinium Derivatives with Alkyl Bromides

et al. 2020

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“…P yridines are important substructures of natural products, 1 pharmaceuticals, 2 agrochemicals, 3 functional materials, 4 and ligands in catalysis. 5 They are often recognized as "privileged" scaffolds in medicinal chemistry for discovery and optimization of new synthetic drug molecules. Currently, over 100 marketed pharmaceuticals, including drugs such as Nexium (anti-acid) and Imatinib (anti-cancer), bear at least one pyridine ring.…”

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confidence: 99%

β-Selective Reductive Coupling of Alkenylpyridines with Aldehydes and Imines via Synergistic Lewis Acid/Photoredox Catalysis

2017

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Umpolung (polarity reversal) strategies of aldehydes and imines have dramatically expanded the scope of carbonyl and iminyl chemistry by facilitating reactions with non-nucleophilic reagents. Herein, we report the first visible light photoredox-catalyzed β-selective reductive coupling of alkenylpyridines with carbonyl or iminyl derivatives with the aid of a Lewis acid co-catalyst. Our process tolerates complex molecular scaffolds (e.g. sugar, natural product, and peptide derivatives) and is applicable to the preparation of compounds containing a broad range of heterocyclic moieties. Mechanistic investigations indicate that the key step involves single electron transfer (SET) reduction of aldehydes or imines followed by the addition of resulting ketyl or α-aminoalkyl radicals to Lewis acid-activated alkenylpyridines.

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“…2 Fur-thermore, pyridines have important uses as ligands for coordination complexes and as organocatalysts. 3,4 They are also emerging as redox active molecules in battery applications and are encountered in materials such as pillaring struts in metal organic frameworks. 5,6 Importantly, it is the combined effect of the pyridine nucleus and the adorning substituents that give rise to such a wide range of applications.…”

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confidence: 99%

4-Selective Pyridine Functionalization Reactions via Heterocyclic Phosphonium Salts

Dolewski

Hilton

McNally

2017

Synlett

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Pyridines are widely used across the chemical sciences in applications ranging from pharmaceuticals, ligands for metal complex and battery technologies. Direct functionalization of pyridine C–H bonds is an important strategy to make useful pyridine derivatives, but there are few ways to selectively transform the 4-position of the scaffold. We recently reported that pyridines can be converted into heterocyclic phosphonium salts that can serve as generic handles for multiple subsequent bond-forming processes. Reactions with nucleophiles and transition-metal cross-couplings will be described to make C–O, C–S, C–N, and C–C bonds in a diverse range of pyridines including those embedded in complex pharmaceuticals.1 Introduction2 Direct, Regioselective Functionalization of Pyridines3 4-Position Selectivity via Metal Catalysis4 Versatile Functional Groups versus Specific Bond Constructions5 Phosphonium Salts as Reagents for Pyridine Functionalization6 Conclusions

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ChemInform Abstract: Pyridine and Related Ligands in Transition Metal Homogeneous Catalysis

Abstract: Review: 53 refs.

Cited by 5 publications

References 1 publication

Visible-Light-Driven C4-Selective Alkylation of Pyridinium Derivatives with Alkyl Bromides

Visible-Light-Driven C4-Selective Alkylation of Pyridinium Derivatives with Alkyl Bromides

β-Selective Reductive Coupling of Alkenylpyridines with Aldehydes and Imines via Synergistic Lewis Acid/Photoredox Catalysis

4-Selective Pyridine Functionalization Reactions via Heterocyclic Phosphonium Salts

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