Regioselective Homolytic C²–H Borylation of Unprotected Adenosine and Adenine Derivatives via Minisci Reaction

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(31), С. 21428 - 21441

Опубликована: Июль 25, 2024

A Minisci-type borylation of unprotected adenosine, adenine nucleotide, and adenosine analogues was successfully achieved through photocatalysis or thermal activation. Despite the challenges posed by presence two potential reactive sites (C

Язык: Английский

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Advances in Pyridine C – H Functionalizations: Beyond C2 Selectivity

Chemistry - A European Journal, Год журнала: 2024, Номер 31(2)

Опубликована: Ноя. 28, 2024

The pyridine core is a crucial component in numerous FDA-approved drugs and Environmental Protection Agency (EPA) regulated agrochemicals. It also plays significant role ligands for transition metals, alkaloids, catalysts, various organic materials with diverse properties, making it one of the most important structural frameworks. However, despite its significance, direct selective functionalization still relatively underdeveloped due to electron-deficient nature strong coordinating ability nitrogen. Among variety synthetic transformation, C-H bond straightforward atom economical approach it's advantageous late-stage containing drugs. In recent years, innovative strategies regioselective pyridines azines have emerged, offering benefits such as high regioselectivity, mild conditions, enabling transformations that were challenging traditional methods. This review emphasizes latest advancements meta para-C-H through approaches, including phosphonium salts, photocatalytic methods, temporary de-aromatization, Minisci-type reactions, metal-catalyzed activation techniques. We discuss advantages limitations these current methods aim inspire further progress this field.

Язык: Английский

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Spirobipyridine Ligands as a Unique Platform for Substrate Recognition and Reaction Control through Noncovalent Interactions

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 6372 - 6379

Опубликована: Апрель 4, 2025

Язык: Английский

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Photoinduced C–H Functionalization of Pyridines with N-Functionalized Pyridinium Salts

Topics in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

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Photocatalyst‐ and Transition Metal‐Free Light‐Induced Borylation Reactions

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(21)

Опубликована: Сен. 25, 2023

The increasing global warming concerns have propelled a surge in the demand for sustainable energy sources within domain of synthetic organic chemistry. A particularly prominent area research has been development mild strategies generating heterocyclic compounds. Heterocyclic compounds containing boron notably risen to prominence as pivotal reagents myriad transformations, showcasing their wide-ranging applicability. This comprehensive review is aimed at collecting literature pertaining borylation reactions induced by light, specifically focusing on photocatalyst-free and transition metal-free methodologies. central emphasis delving into selective mechanistic investigations. amalgamation analysis these insights elucidate substantial potential inherent eco-friendly approaches synthesizing compounds, thus propelling landscape

Язык: Английский

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Photoredox-Catalyzed Tandem Cyclization of Enaminones with N-Sulfonylaminopyridinium Salts toward the Synthesis of 3-Sulfonaminated Chromones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 644 - 655

Опубликована: Дек. 13, 2023

A photoredox-catalyzed intermolecular tandem sulfonamination/cyclization of enaminones was realized by using N-aminopyridinium salts as the sulfonaminated reagents without transition-metal catalysts or bases. The reaction exhibits a broad scope and good functional group tolerance, yields, regioselectivity. Preliminary mechanistic studies support radical property involvement N-centered intermediates.

Язык: Английский

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Enhanced Efficiency of Amide‐Substituted Quinuclidine‐Boranes as Hydridic Hydrogen Atom Transfer Catalysts for Photoinduced Hydroalkylation of Unactivated Olefins^†

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 10, 2024

Comprehensive Summary An amide‐substituted quinuclidine‐borane has been identified as a more efficient hydridic hydrogen atom transfer (HAT) catalyst for the hydroalkylation of unactivated olefins under visible‐light irradiation. 1 H NMR titration experiments reveal that amide moiety forms stronger bonds with carbonyl substrates, thereby improving reaction yields. Furthermore, it was found yields correlate well association constant between and substrate. A scale‐up using continuous‐flow photoreactor also demonstrated.

Язык: Английский

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Recent Advances in Methodologies for Radical‐Mechanistic Borylation^†

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 17, 2024

Comprehensive Summary We reviewed works on radical borylation reactions since 2020 from two aspects. 1. Borylation alkyl or aryl radicals : This approach involves the generation of various precursors such as halides and carboxylic acids, followed by their reaction with diboron reagents to form boron esters. 2. boron‐centered generating radicals, which then react substrates achieve borylation. Key Scientists

Язык: Английский

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Recent Advances in Borylation via Electron Donor–Acceptor Complex Photoactivation

ChemPhotoChem, Год журнала: 2023, Номер 7(11)

Опубликована: Июль 19, 2023

Abstract Photoinduced borylation is becoming a fascinating and growing research field in synthetic chemistry. On the other hand, electron donor–acceptor (EDA) complex photoactivation has emerged as an alternative strategy to generate active open‐shell species without need for photosensitizers. Suitable organoboron compounds can serve donor or acceptor form corresponding complexes, which then undergo photoinduced intracomplex single transfer (SET) carbon‐ boron‐centered radicals construction of new C−B bonds. In this Concept paper, we review recent advances via EDA surveying relevant literature until December 2022.

Язык: Английский

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An electron-donor–acceptor complex between two intermediates enables a N–N bond cleavage cascade process to access 2,3-difunctionalized pyridines

Green Chemistry, Год журнала: 2024, Номер 26(4), С. 2280 - 2289

Опубликована: Янв. 1, 2024

A visible-light-enabled catalyst-free [3 + 2] cycloaddition/N–N bond cleavage/intramolecular C–N formation cascade process to access 2,3-difunctionalized pyridines was developed.

Язык: Английский

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